Compound characterization data — Strähler et al., 2026

Sebastian Strähler, Anthony Kromodimedjo, Rens Clijnk, Ümeyr Tasova, Remco Broersen, H. Daniël Preschel, Olivier Riant, Eelco Ruijter. “Sequential dual catalysis merging enantioselective Cu-catalyzed conjugate addition with intramolecular Pd/Ir-catalyzed allylic alkylation.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007440/v1

3-ethoxycyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.34 (s, 1H), 3.90 (q, J = 7.0 Hz, 2H), 2.40 (t, J = 6.3 Hz, 2H), 2.34 (d, J = 6.2 Hz, 2H), 1.97 (p, J = 6.4 Hz, 2H), 1.36 (t, J = 7.0 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 178.1, 102.8, 64.3, 36.9, 29.2, 21.4, 14.2

3-ethoxy-5,5-dimethylcyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.32 (s, 1H), 3.89 (q, J = 7.0 Hz, 2H), 2.25 (s, 2H), 2.19 (s, 2H), 1.35 (t, J = 7.0 Hz, 3H), 1.05 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.7, 176.3, 101.6, 64.3, 50.9, 43.1, 32.6, 28.4, 14.2

3-ethoxy-6,6-dimethylcyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.24 (s, 1H), 3.88 (q, J = 7.0 Hz, 2H), 2.42 (t, J = 6.4 Hz, 2H), 1.80 (td, J = 6.3, 1.2 Hz, 2H), 1.35 (td, J = 7.0, 1.2 Hz, 3H), 1.11 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 204.7, 175.9, 101.2, 64.3, 40.3, 35.2, 26.5, 24.7, 14.3

3-ethoxy-4,4-dimethylcyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.22 (s, 1H), 3.86 (q, J = 7.0 Hz, 2H), 2.39 (t, J = 6.7 Hz, 2H), 1.82 (t, J = 7.0 Hz, 2H), 1.35 (t, J = 7.0 Hz, 3H), 1.19 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 183.2, 101.3, 64.3, 36.4, 35.8, 33.9, 25.8, 14.1

3-ethoxycyclopent-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.27 (s, 1H), 4.03 (q, J = 7.1 Hz, 2H), 2.61 – 2.57 (m, 2H), 2.45 – 2.36 (m, 2H), 1.39 (t, J = 7.1 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 206.2, 190.2, 104.8, 67.8, 34.1, 28.7, 14.3

3-ethoxycyclohept-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.37 (s, 1H), 3.79 (q, J = 7.0 Hz, 2H), 2.62 – 2.52 (m, 4H), 1.88 – 1.76 (m, 4H), 1.33 (t, J = 7.0 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 202.6, 176.4, 105.9, 64.3, 41.8, 33.2, 23.6, 21.4, 14.4

3-(but-3-en-1-yl)cyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.88 (s, 1H), 5.78 (ddt, J = 16.3, 10.2, 6.2 Hz, 1H), 5.09 – 4.98 (m, 2H), 2.36 (d, J = 6.8 Hz, 2H), 2.34 – 2.23 (m, 6H), 1.99 (d, J = 6.5 Hz, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.0, 165.6, 137.1, 126.1, 115.7, 37.5, 37.4, 31.1, 29.9, 22.8

3-(pent-4-en-1-yl)cyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.87 (s, 1H), 5.78 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.06 – 4.94 (m, 2H), 2.35 (d, J = 6.9 Hz, 2H), 2.27 (t, J = 5.9 Hz, 2H), 2.21 (d, J = 7.9 Hz, 2H), 2.07 (q, J = 7.2 Hz, 2H), 1.98 (p, J = 6.2 Hz, 2H), 1.60 (p, J = 7.5 Hz, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.0, 166.3, 138.0, 125.9, 115.4, 37.5, 33.3, 29.8, 26.2, 22.9

3-(4-methylpent-3-en-1-yl)cyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.88 (s, 1H), 5.07 (t, J = 6.8 Hz, 1H), 2.35 (t, J = 6.9 Hz, 2H), 2.28 (t, J = 6.1 Hz, 2H), 2.26 – 2.15 (m, 4H), 1.98 (p, J = 6.2 Hz, 2H), 1.68 (s, 3H), 1.60 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.1, 166.3, 132.9, 125.9, 122.8, 38.2, 37.5, 29.9, 25.8, 25.7, 22.8, 17.8

5,5-dimethyl-3-(pent-4-en-1-yl)cyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.88 (s, 1H), 5.78 (ddt, J = 16.9, 10.2, 6.6 Hz, 1H), 5.07 – 4.92 (m, 2H), 2.24 – 2.14 (m, 6H), 2.12 – 2.03 (m, 2H), 1.63 – 1.55 (m, 2H), 1.03 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.2, 163.9, 138.0, 124.9, 115.4, 51.2, 44.1, 37.5, 33.7, 33.3, 28.4, 26.1

6,6-dimethyl-3-(pent-4-en-1-yl)cyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.87 – 5.71 (m, 2H), 5.09 – 4.94 (m, 2H), 2.43 (t, J = 7.0 Hz, 2H), 2.24 – 2.16 (m, 2H), 2.14 – 2.03 (m, 2H), 1.86 – 1.83 (m, 2H), 1.59 (p, J = 7.4 Hz, 2H), 1.16 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.6, 172.6, 138.1, 124.5, 115.3, 38.1, 35.8, 34.4, 33.5, 31.4, 26.7, 26.6

3-(pent-4-en-1-yl)cyclopent-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.96 – 5.93 (m, 1H), 5.79 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.06 – 4.98 (m, 2H), 2.60 – 2.55 (m, 2H), 2.44 – 2.38 (m, 4H), 2.15 – 2.08 (m, 2H), 1.73 – 1.65 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 210.2, 182.8, 137.8, 129.7, 115.6, 35.4, 33.4, 32.9, 31.7, 26.3

3-(pent-4-en-1-yl)cyclohept-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.90 (s, 1H), 5.83 – 5.73 (m, 1H), 5.05 – 4.95 (m, 2H), 2.57 (t, J = 6.2 Hz, 2H), 2.40 (t, J = 5.9 Hz, 2H), 2.19 (t, J = 7.8 Hz, 2H), 2.07 (q, J = 7.5 Hz, 2H), 1.83 – 1.74 (m, 4H), 1.58 (p, J = 7.4 Hz, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 204.2, 162.0, 138.1, 129.5, 115.3, 42.3, 40.5, 33.4, 32.7, 26.9, 25.3, 21.4
IR (neat) νmax (cm⁻¹)	2930, 1655, 1630, 1458, 1259, 991, 910, 881, 627, 511, 467
HRMS (ESI)	m/z calcd. for C₁₂H₁₉O⁺ [M + H]⁺ 179.1430, found 179.1425

Allyl methyl carbonate
¹H NMR (500 MHz, CDCl₃)	δ 5.94 (ddt, J = 17.1, 10.5, 5.8 Hz, 1H), 5.36 (dq, J = 17.2, 1.5 Hz, 1H), 5.27 (dq, J = 10.5, 1.1 Hz, 1H), 4.63 (dt, J = 5.8, 1.3 Hz, 2H), 3.80 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 155.7, 131.7, 119.0, 68.6, 54.9

Allyl tert-butyl carbonate
¹H NMR (500 MHz, CDCl₃)	δ 5.93 (ddt, J = 17.1, 10.4, 5.8 Hz, 1H), 5.34 (dq, J = 17.2, 1.5 Hz, 1H), 5.25 (dq, J = 10.4, 1.3 Hz, 1H), 4.56 (dt, J = 5.8, 1.4 Hz, 2H), 1.49 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 153.4, 132.1, 118.7, 82.3, 67.7, 27.9

Z-but-2-ene-1,4-diyl diacetate
¹H NMR (500 MHz, CDCl₃)	δ 5.79 – 5.70 (m, 2H), 4.71 – 4.64 (m, 4H), 2.06 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.9, 128.2, 60.1, 21.0

2-methylallyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 4.97 (s, 1H), 4.92 (s, 1H), 4.49 (s, 2H), 2.09 (s, 3H), 1.76 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.9, 140.1, 113.0, 67.9, 21.0, 19.6

2-(((tert-butyldiphenylsilyl)oxy)methyl)prop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.68 (dd, J = 8.0, 1.4 Hz, 4H), 7.46 – 7.37 (m, 6H), 5.14 (d, J = 18.7 Hz, 2H), 4.26 (s, 2H), 4.19 (s, 2H), 1.07 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 147.3, 135.7, 133.4, 129.9, 127.9, 111.3, 65.7, 64.7, 27.0, 19.4

2-(((tert-butyldiphenylsilyl)oxy)methyl)allyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.70 – 7.65 (m, 4H), 7.46 – 7.36 (m, 6H), 5.32 (s, 1H), 5.17 (s, 1H), 4.59 (s, 2H), 4.20 (s, 2H), 2.02 (s, 3H), 1.06 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.8, 143.0, 135.7, 133.5, 129.9, 127.9, 113.3, 64.9, 64.6, 26.9, 21.0, 19.4
IR (neat) νmax (cm⁻¹)	1742, 1427, 1230, 1107, 1028, 822, 739, 700, 608, 505, 488
HRMS (ESI)	m/z calcd. for C₂₂H₂₉O₃Si⁺ [M + H]⁺ 369.1880, found 369.1906

5-(methylthio)pent-1-en-3-ol
¹H NMR (500 MHz, CDCl₃)	δ 5.87 (ddd, J = 17.1, 10.4, 6.0 Hz, 1H), 5.26 (dt, J = 17.2, 1.4 Hz, 1H), 5.13 (dt, J = 10.4, 1.3 Hz, 1H), 4.30 – 4.24 (m, 1H), 2.60 (t, J = 7.2 Hz, 2H), 2.11 (s, 3H), 1.92 (br s, 1H), 1.85 – 1.78 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 140.6, 115.2, 72.2, 35.9, 30.4, 15.6
IR (neat) νmax (cm⁻¹)	2916, 2359, 2341, 2260, 1423, 1038, 991, 922
HRMS (ESI)	m/z calcd. for C₆H₁₃OS⁺ [M + H]⁺ 133.0682, found 133.0691

5-(methylthio)pent-1-en-3-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.77 (ddd, J = 17.1, 10.5, 6.4 Hz, 1H), 5.36 – 5.30 (m, 1H), 5.26 (dt, J = 17.2, 1.3 Hz, 1H), 5.19 (dt, J = 10.5, 1.2 Hz, 1H), 2.51 – 2.46 (m, 2H), 2.09 (s, 3H), 2.06 (s, 3H), 1.99 – 1.83 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.3, 135.9, 117.3, 73.7, 33.9, 29.8, 21.3, 15.6

1-(furan-2-yl)prop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.40 (dd, J = 1.8, 0.9 Hz, 1H), 6.34 (dd, J = 3.3, 1.8 Hz, 1H), 6.26 (dt, J = 3.3, 0.8 Hz, 1H), 6.13 (ddd, J = 17.1, 10.4, 5.7 Hz, 1H), 5.43 (dt, J = 17.1, 1.4 Hz, 1H), 5.29 (dt, J = 10.4, 1.4 Hz, 1H), 5.23 (t, J = 5.1 Hz, 1H), 2.05 (d, J = 5.0 Hz, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 155.1, 142.6, 136.9, 116.7, 110.4, 106.9, 68.8

1-(furan-2-yl)allyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.41 (dd, J = 1.6, 1.1 Hz, 1H), 6.36 – 6.32 (m, 3H), 6.07 (ddd, J = 16.9, 10.4, 6.2 Hz, 1H), 5.40 (dt, J = 17.2, 1.2 Hz, 1H), 5.33 (dt, J = 10.5, 1.2 Hz, 1H), 2.10 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.0, 151.5, 143.2, 133.0, 118.5, 110.5, 109.2, 69.2, 21.2

1-phenylprop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.40 – 7.27 (m, 5H), 6.11 – 6.01 (m, 1H), 5.39 – 5.34 (m, 1H), 5.23 – 5.18 (m, 2H), 1.94 (br s, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 142.7, 140.4, 128.7, 127.9, 126.5, 115.3, 75.5

1-phenylallyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.39 – 7.29 (m, 5H), 6.27 (d, J = 5.9 Hz, 1H), 6.01 (ddd, J = 17.0, 10.4, 5.9 Hz, 1H), 5.33 – 5.22 (m, 2H), 2.12 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.1, 139.0, 136.4, 128.7, 128.3, 127.3, 117.0, 76.3, 21.4

1-(4-methoxyphenyl)prop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.35 – 7.27 (m, 2H), 6.93 – 6.85 (m, 2H), 6.05 (ddd, J = 17.1, 10.3, 5.8 Hz, 1H), 5.34 (dt, J = 17.1, 1.4 Hz, 1H), 5.19 (dt, J = 10.3, 1.4 Hz, 1H), 5.16 (d, J = 5.7 Hz, 1H), 3.80 (s, 3H), 1.97 (s, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 159.3, 140.5, 135.0, 127.8, 114.9, 114.1, 75.0, 55.4

1-(4-methoxyphenyl)allyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.32 – 7.27 (m, 2H), 6.91 – 6.86 (m, 2H), 6.23 (d, J = 5.7 Hz, 1H), 6.01 (ddd, J = 17.1, 10.5, 5.7 Hz, 1H), 5.31 – 5.20 (m, 2H), 3.80 (s, 3H), 2.09 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.2, 159.6, 136.5, 131.1, 128.8, 116.6, 114.0, 76.0, 55.4, 21.4

1-(4-fluorophenyl)prop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.39 – 7.31 (m, 2H), 7.08 – 6.99 (m, 2H), 6.02 (ddd, J = 17.1, 10.3, 6.0 Hz, 1H), 5.34 (dt, J = 17.1, 1.4 Hz, 1H), 5.26 – 5.13 (m, 2H), 2.06 (s, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 162.4 (d, JC-F = 245.8 Hz), 140.2, 138.4 (d, JC-F = 3.1 Hz), 128.2 (d, JC-F = 8.1 Hz), 115.48, 115.48 (d, JC-F = 21.4 Hz), 74.8

1-(4-fluorophenyl)allyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.37 – 7.29 (m, 2H), 7.07 – 7.00 (m, 2H), 6.24 (d, J = 5.8 Hz, 1H), 5.98 (ddd, J = 17.1, 10.5, 5.8 Hz, 1H), 5.31 – 5.22 (m, 2H), 2.10 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.1, 162.6 (d, J = 246.7 Hz), 136.2, 134.9 (d, J = 3.2 Hz), 129.2 (d, J = 8.3 Hz), 117.2, 115.6 (d, J = 21.5 Hz), 75.6, 21.3

1-(4-chlorophenyl)prop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.35 – 7.28 (m, 4H), 6.06 – 5.93 (m, 1H), 5.34 (dt, J = 17.1, 1.3 Hz, 1H), 5.21 (dt, J = 10.3, 1.2 Hz, 1H), 5.18 (d, J = 6.1 Hz, 1H), 2.03 (s, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 141.1, 140.0, 133.6, 128.8, 127.8, 115.8, 74.8

1-(4-chlorophenyl)allyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.34 – 7.27 (m, 4H), 6.22 (d, J = 5.8 Hz, 1H), 5.97 (ddd, J = 17.1, 10.5, 5.9 Hz, 1H), 5.31 – 5.23 (m, 2H), 2.11 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.0, 137.5, 136.0, 134.1, 128.9, 128.7, 117.5, 75.6, 21.3

1-(3-chlorophenyl)prop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.40 – 7.35 (m, 1H), 7.30 – 7.22 (m, 3H), 6.00 (ddd, J = 17.0, 10.3, 6.2 Hz, 1H), 5.35 (dt, J = 17.1, 1.3 Hz, 1H), 5.22 (dt, J = 10.3, 1.2 Hz, 1H), 5.17 (d, J = 6.1 Hz, 1H), 2.07 (br s, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 144.6, 139.8, 134.6, 129.9, 127.9, 126.6, 124.6, 116.0, 74.9

1-(3-chlorophenyl)allyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.36 – 7.33 (m, 1H), 7.31 – 7.27 (m, 2H), 7.25 – 7.21 (m, 1H), 6.22 (d, J = 6.0 Hz, 1H), 5.96 (ddd, J = 17.2, 10.4, 6.0 Hz, 1H), 5.33 – 5.25 (m, 2H), 2.13 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 169.9, 141.1, 135.8, 134.6, 130.0, 128.4, 127.3, 125.4, 117.7, 75.5, 21.3
IR (neat) νmax (cm⁻¹)	2357, 1740, 1369, 1223, 1198, 1022, 984, 935, 785, 694, 611
HRMS (ESI)	m/z calcd. for C₁₁H₁₁ClO₂Na⁺ [M + Na]⁺ 233.0340, found 233.0337

1-(2-chlorophenyl)prop-2-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.54 (dd, J = 7.7, 1.7 Hz, 1H), 7.35 (dd, J = 7.9, 1.3 Hz, 1H), 7.29 (td, J = 7.5, 1.2 Hz, 1H), 7.22 (td, J = 7.6, 1.7 Hz, 1H), 6.04 (ddd, J = 17.1, 10.4, 5.5 Hz, 1H), 5.64 (d, J = 4.1 Hz, 1H), 5.39 (dt, J = 17.2, 1.4 Hz, 1H), 5.22 (dt, J = 10.4, 1.4 Hz, 1H), 2.21 (d, J = 2.5 Hz, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 140.0, 138.5, 132.5, 129.7, 128.9, 127.8, 127.3, 115.7, 71.6

1-(2-chlorophenyl)allyl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.44 (dd, J = 7.6, 1.8 Hz, 1H), 7.37 (dd, J = 7.8, 1.4 Hz, 1H), 7.28 (td, J = 7.5, 1.4 Hz, 1H), 7.24 (td, J = 7.6, 1.9 Hz, 1H), 6.64 (d, J = 5.7 Hz, 1H), 5.99 (ddd, J = 17.1, 10.5, 5.7 Hz, 1H), 5.31 – 5.24 (m, 2H), 2.13 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 169.7, 136.8, 134.8, 133.0, 129.8, 129.3, 128.1, 127.2, 117.5, 72.9, 21.2

8-vinyl-1,4-dioxaspiro[4.5]decan-8-ol
¹H NMR (500 MHz, CDCl₃)	δ 5.95 (dd, J = 17.3, 10.8 Hz, 1H), 5.25 (dd, J = 17.4, 1.2 Hz, 1H), 5.02 (dd, J = 10.7, 1.2 Hz, 1H), 3.96 – 3.87 (m, 4H), 1.97 – 1.88 (m, 2H), 1.81 – 1.72 (m, 2H), 1.65 – 1.54 (m, 4H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 145.5, 112.0, 108.6, 70.9, 64.35, 64.27, 35.1, 30.5

8-vinyl-1,4-dioxaspiro[4.5]decan-8-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 6.10 (dd, J = 17.6, 11.0 Hz, 1H), 5.18 (dd, J = 17.6, 0.7 Hz, 1H), 5.14 (dd, J = 11.1, 0.8 Hz, 1H), 3.98 – 3.91 (m, 4H), 2.33 – 2.26 (m, 2H), 2.02 (s, 3H), 1.86 – 1.74 (m, 4H), 1.67 – 1.58 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.1, 140.9, 114.1, 108.2, 80.8, 64.5, 64.4, 32.4, 30.6, 22.1
IR (neat) νmax (cm⁻¹)	1734, 1445, 1371, 1261, 1225, 1095, 1034, 947, 918, 631, 586, 530, 492
HRMS (ESI)	m/z calcd. for C₁₂H₁₈O₄Na⁺ [M + Na]⁺ 249.1097, found 249.1096

E-tert-butyl((3,7-dimethylocta-2,6-dien-1-yl)oxy)diphenylsilane
¹H NMR (500 MHz, CDCl₃)	δ 7.75 – 7.69 (m, 4H), 7.46 – 7.36 (m, 6H), 5.42 – 5.37 (m, 1H), 5.14 – 5.09 (m, 1H), 4.25 – 4.22 (m, 2H), 2.11 – 2.04 (m, 2H), 2.02 – 1.96 (m, 2H), 1.70 (d, J = 1.2 Hz, 3H), 1.63 – 1.61 (m, 3H), 1.45 (d, J = 0.8 Hz, 3H), 1.06 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 137.2, 135.8, 134.3, 131.6, 129.6, 127.7, 124.3, 124.2, 61.3, 39.6, 27.0, 26.5, 25.8, 19.3, 17.9, 16.5

E-tert-butyl((5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)oxy)diphenylsilane
¹H NMR (500 MHz, CDCl₃)	δ 7.72 – 7.67 (m, 4H), 7.43 – 7.36 (m, 6H), 5.45 – 5.39 (m, 1H), 4.23 (d, J = 6.3 Hz, 2H), 2.71 (t, J = 6.3 Hz, 1H), 2.19 – 2.04 (m, 2H), 1.70 – 1.56 (m, 2H), 1.47 (s, 3H), 1.31 (s, 3H), 1.27 (s, 3H), 1.05 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 136.3, 135.7, 134.1, 129.7, 127.7, 124.8, 64.2, 61.2, 58.5, 36.2, 27.3, 27.0, 25.0, 19.3, 18.9, 16.5

E-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-4-enal
¹H NMR (500 MHz, CDCl₃)	δ 9.75 (t, J = 1.8 Hz, 1H), 7.71 – 7.67 (m, 4H), 7.44 – 7.36 (m, 6H), 5.39 (tq, J = 6.2, 1.3 Hz, 1H), 4.24 – 4.21 (m, 2H), 2.50 (td, J = 7.5, 1.6 Hz, 2H), 2.30 (t, J = 7.5 Hz, 2H), 1.45 (s, 3H), 1.05 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 202.3, 135.7, 135.1, 134.1, 129.7, 127.7, 125.2, 61.1, 42.0, 31.6, 27.0, 19.3, 16.6

E-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-4-en-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 7.71 – 7.67 (m, 4H), 7.44 – 7.35 (m, 6H), 5.41 (tq, J = 6.3, 1.3 Hz, 1H), 4.22 (d, J = 5.9 Hz, 2H), 3.62 (t, J = 6.5 Hz, 2H), 2.05 (t, J = 7.6 Hz, 2H), 1.70 – 1.63 (m, 2H), 1.46 (s, 3H), 1.04 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 137.0, 135.8, 134.2, 129.7, 127.7, 124.6, 62.9, 61.2, 35.9, 30.7, 27.0, 19.3, 16.3

E-((6-bromo-3-methylhex-2-en-1-yl)oxy)(tert-butyl)diphenylsilane
¹H NMR (500 MHz, CDCl₃)	δ 7.72 – 7.65 (m, 4H), 7.44 – 7.36 (m, 6H), 5.43 – 5.39 (m, 1H), 4.22 (d, J = 6.2 Hz, 2H), 3.36 (t, J = 6.8 Hz, 2H), 2.10 (t, J = 7.4 Hz, 2H), 1.93 (p, J = 6.9 Hz, 2H), 1.43 (s, 3H), 1.04 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 135.7, 135.2, 134.1, 129.7, 127.7, 125.5, 61.1, 37.8, 33.5, 30.8, 27.0, 19.3, 16.3
HRMS (ESI)	m/z calcd. for C₂₃H₃₂BrOSi⁺ [M + H]⁺ 431.1400, found 431.1397

E-3-(6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-4-en-1-yl)cyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 7.72 – 7.68 (m, 4H), 7.44 – 7.35 (m, 6H), 5.88 (s, 1H), 5.38 (tq, J = 6.3, 1.3 Hz, 1H), 4.23 (d, J = 6.3 Hz, 2H), 2.37 (d, J = 7.0 Hz, 2H), 2.27 (t, J = 5.9 Hz, 2H), 2.17 (d, J = 7.6 Hz, 2H), 1.99 (p, J = 6.0 Hz, 4H), 1.59 (p, J = 7.6 Hz, 2H), 1.44 (s, 3H), 1.05 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 166.4, 136.3, 135.7, 134.1, 129.6, 127.7, 125.8, 124.9, 61.1, 38.9, 37.5, 37.5, 29.9, 27.0, 24.9, 22.9, 19.3, 16.3
IR (neat) νmax (cm⁻¹)	2934, 2856, 2361, 1668, 1649, 1427, 1109, 1067, 1051, 822, 739, 700, 689, 608, 503, 490
HRMS (ESI)	m/z calcd. for C₂₉H₃₉O₂Si⁺ [M + H]⁺ 447.2714, found 447.2712

E-3-(6-hydroxy-4-methylhex-4-en-1-yl)cyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.82 (s, 1H), 5.36 (tq, J = 6.8, 1.4 Hz, 1H), 4.10 (d, J = 6.8 Hz, 2H), 2.30 (d, J = 7.4 Hz, 2H), 2.24 (t, J = 6.0 Hz, 2H), 2.15 (d, J = 7.4 Hz, 2H), 2.10 (br s, 1H), 1.98 (t, J = 7.6 Hz, 2H), 1.93 (p, J = 6.2 Hz, 2H), 1.61 (s, 3H), 1.60 – 1.55 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.2, 166.6, 138.2, 125.7, 124.4, 59.1, 38.9, 37.5, 37.3, 29.7, 24.8, 22.7, 16.1
IR (neat) νmax (cm⁻¹)	2937, 1655, 1622, 1454, 1427, 1416, 1375, 1348, 1325, 1256, 1192, 1005, 999, 966, 889
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O₂⁺ [M + H]⁺ 209.1536, found 209.1537

E-3-methyl-6-(3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.87 – 5.85 (m, 1H), 5.36 – 5.30 (m, 1H), 4.57 (d, J = 7.0 Hz, 2H), 2.35 (d, J = 6.2 Hz, 2H), 2.27 (t, J = 5.9 Hz, 2H), 2.18 (d, J = 8.1 Hz, 2H), 2.07 – 2.01 (m, 5H), 1.98 (p, J = 6.2 Hz, 2H), 1.68 (s, 3H), 1.63 (p, J = 7.6 Hz, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.0, 171.2, 166.1, 141.4, 125.9, 119.2, 61.4, 39.0, 37.54, 37.45, 29.8, 24.8, 22.8, 21.2, 16.4
IR (neat) νmax (cm⁻¹)	2939, 1732, 1664, 1624, 1367, 1229, 1192, 1022, 964, 953, 889
HRMS (ESI)	m/z calcd. for C₁₅H₂₃O₃⁺ [M + H]⁺ 251.1642, found 251.1635

6-allyl-3-ethoxycyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.83 – 5.73 (m, 1H), 5.33 (s, 1H), 5.09 – 5.01 (m, 2H), 3.96 – 3.83 (m, 2H), 2.68 – 2.61 (m, 1H), 2.48 – 2.36 (m, 2H), 2.29 – 2.21 (m, 1H), 2.18 – 2.02 (m, 2H), 1.77 – 1.65 (m, 1H), 1.36 (t, J = 7.0 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.8, 177.2, 136.5, 116.8, 102.4, 64.4, 44.8, 34.2, 28.3, 25.9, 14.3

4-allyl-3-methylcyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 5.85 (s, 1H), 5.83 – 5.74 (m, 1H), 5.16 – 5.06 (m, 2H), 2.47 – 2.39 (m, 2H), 2.37 – 2.16 (m, 3H), 2.07 – 2.00 (m, 1H), 1.98 (s, 3H), 1.95 – 1.87 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.5, 165.1, 136.2, 127.2, 117.5, 39.3, 35.8, 33.9, 26.5, 23.1

4-(2-methyl-4-oxocyclohex-2-en-1-yl)but-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.85 (s, 1H), 5.77 – 5.60 (m, 2H), 4.53 (d, J = 5.7 Hz, 2H), 2.46 – 2.37 (m, 2H), 2.37 – 2.17 (m, 3H), 2.08 – 2.00 (m, 1H), 2.06 (s, 3H), 1.97 (s, 3H), 1.91 – 1.82 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.3, 170.9, 164.6, 133.1, 127.4, 127.0, 64.8, 39.3, 34.2, 33.9, 26.5, 23.1, 21.1
IR (neat) νmax (cm⁻¹)	1734, 1666, 1653, 1624, 1441, 1379, 1364, 1227, 1024, 968, 856, 505
HRMS (ESI)	m/z calcd. for C₁₃H₁₉O₃⁺ [M + H]⁺ 223.1329, found 223.1328

4-(2-methyl-4-oxocyclohex-2-en-1-yl)-1-phenylbut-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.38 – 7.28 (m, 10H), 6.24 (dd, J = 5.8, 4.1 Hz, 2H), 5.84 (s, 2H), 5.77 – 5.67 (m, 4H), 2.47 – 2.15 (m, 10H), 2.10 (s, 3H), 2.10 (s, 3H), 2.06 – 1.98 (m, 2H), 1.95 (d, J = 1.3 Hz, 3H), 1.94 (d, J = 1.5 Hz, 3H), 1.88 – 1.80 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.28, 199.26, 170.13 (2C), 164.66, 164.64, 139.39, 139.33, 131.58 (2C), 131.34 (2C), 128.73 (2C), 128.27 (2C), 128.25 (2C), 127.37 (2C), 127.35 (2C), 126.98, 126.94, 76.03, 75.95, 39.36, 39.31, 34.26 (2C), 33.89, 33.88, 26.64, 26.59, 23.14, 23.12, 21.45 (2C)
IR (neat) νmax (cm⁻¹)	1732, 1666, 1371, 1229, 1203, 1016, 966, 754, 733, 698, 540, 457
HRMS (ESI)	m/z calcd. for C₁₉H₂₂O₃Na⁺ [M + Na]⁺ 321.1461, found 321.1433

Z-4-hydroxybut-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.89 – 5.82 (m, 1H), 5.66 – 5.59 (m, 1H), 4.67 (d, J = 7.1 Hz, 2H), 4.25 (t, J = 6.1 Hz, 2H), 2.06 (s, 3H), 2.07 – 2.01 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 171.3, 133.5, 125.7, 60.3, 58.5, 21.1

Z-4-bromobut-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 6.01 – 5.89 (m, 1H), 5.76 – 5.63 (m, 1H), 4.69 (dd, J = 6.9, 1.5 Hz, 2H), 4.02 (dd, J = 8.4, 0.8 Hz, 2H), 2.08 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 170.8, 129.9, 128.3, 59.3, 25.8, 21.0

N-(2-bromoethyl)-4-methylbenzenesulfonamide
¹H NMR (500 MHz, CDCl₃)	δ 7.77 – 7.74 (m, 2H), 7.33 (d, J = 8.0 Hz, 2H), 4.86 (s, 1H), 3.44 – 3.34 (m, 4H), 2.44 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 144.0, 137.0, 130.0, 127.2, 44.7, 31.9, 21.7

2-iodo-3-methylcyclohex-2-en-1-one
¹H NMR (500 MHz, CDCl₃)	δ 2.62 – 2.57 (m, 2H), 2.54 (t, J = 6.0 Hz, 2H), 2.25 (s, 3H), 2.01 – 1.95 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 192.2, 166.7, 107.0, 36.5, 34.4, 32.0, 22.3

4-methyl-N-(2-(2-methyl-6-oxocyclohex-1-en-1-yl)ethyl)benzenesulfonamide
¹H NMR (500 MHz, CDCl₃)	δ 7.72 – 7.70 (m, 2H), 7.28 (d, J = 7.9 Hz, 2H), 4.77 (t, J = 5.6 Hz, 1H), 2.97 (q, J = 6.8 Hz, 2H), 2.46 (t, J = 6.8 Hz, 2H), 2.41 (s, 3H), 2.37 – 2.28 (m, 4H), 1.93 (s, 3H), 1.92 – 1.86 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 158.8, 143.3, 137.3, 132.1, 129.7, 127.2, 42.6, 37.7, 33.0, 25.5, 22.1, 21.6, 21.5
IR (neat) νmax (cm⁻¹)	1639, 1624, 1327, 1161, 1082, 818, 696, 582, 551, 540, 494
HRMS (ESI)	m/z calcd. for C₁₆H₂₂NO₃S⁺ [M + H]⁺ 308.1315, found 308.1320

Z-4-((4-methyl-N-(2-(2-methyl-6-oxocyclohex-1-en-1-yl)ethyl)phenyl)sulfonamido)but-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.70 – 7.66 (m, 2H), 7.28 (d, J = 8.0 Hz, 2H), 5.70 – 5.64 (m, 1H), 5.53 – 5.47 (m, 1H), 4.66 (dd, J = 6.9, 1.4 Hz, 2H), 3.93 (dd, J = 6.9, 1.5 Hz, 2H), 3.08 – 3.02 (m, 2H), 2.57 – 2.52 (m, 2H), 2.41 (s, 3H), 2.34 (t, J = 6.7 Hz, 4H), 2.05 (s, 3H), 2.00 (s, 3H), 1.91 (p, J = 6.3 Hz, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 198.6, 170.9, 158.1, 143.3, 137.2, 132.0, 129.8, 129.5, 127.6, 127.3, 59.9, 46.7, 45.1, 37.7, 33.0, 25.4, 22.2, 21.6, 21.6, 21.0
IR (neat) νmax (cm⁻¹)	1736, 1659, 1651, 1373, 1338, 1227, 1155, 1119, 1092, 1026, 816, 658, 546
HRMS (ESI)	m/z calcd. for C₂₂H₃₀NO₅S⁺ [M + H]⁺ 420.1839, found 420.1842

(11bR)-N,N-bis((S)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.94 (d, J = 8.8 Hz, 2H), 7.92 – 7.87 (m, 2H), 7.58 (d, J = 8.8 Hz, 1H), 7.44 – 7.36 (m, 4H), 7.29 – 7.20 (m, 3H), 7.15 – 7.06 (m, 10H), 4.56 – 4.42 (m, 2H), 1.72 (d, J = 7.1 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 150.2 (d, J = 7.4 Hz), 149.7, 143.0, 132.9 (d, J = 7.4 Hz), 131.5, 130.6, 130.4, 129.6, 128.4, 128.2, 128.1 (d, J = 2.3 Hz), 127.9, 127.3, 127.2, 126.8, 126.12, 126.09, 124.9, 124.6, 124.2 (d, J = 5.2 Hz), 122.6, 122.53, 122.52, 121.9 (d, J = 2.3 Hz), 52.4 (d, J = 12.2 Hz), 22.1
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 145.3
IR (neat) νmax (cm⁻¹)	1232, 947, 821, 761, 748, 738, 696, 680, 625, 551
HRMS (ESI)	m/z calcd. for C₃₆H₃₁NO₂P⁺ [M + H]⁺ 540.2092, found 540.2095
Optical rotation	[α]D20 = -424° (c = 1.0, CHCl3)

N,N-bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.50 – 7.46 (m, 2H), 7.38 – 7.19 (m, 6H), 7.17 – 7.09 (m, 10H), 4.65 – 4.54 (m, 2H), 1.74 (d, J = 7.1 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 152.1 (d, J = 8.4 Hz), 151.2 (d, J = 2.6 Hz), 143.1, 131.4 (d, J = 3.8 Hz), 130.1, 130.0, 129.3, 129.1, 128.09, 128.07, 127.9, 126.8, 124.8, 124.1, 122.7 (d, J = 1.6 Hz), 122.2, 52.8 (d, J = 11.7 Hz), 22.4 (d, J = 9.7 Hz)
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 146.3
IR (neat) νmax (cm⁻¹)	889, 777, 752, 731, 694, 611, 542, 525
HRMS (ESI)	m/z calcd. for C₂₈H₂₇NO₂P⁺ [M + H]⁺ 440.1774, found 440.1785
Optical rotation	[α]D20 = -234° (c = 1.0, CHCl3)

2,4,8,10-tetramethyl-N,N-bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.16 – 6.98 (m, 14H), 4.76 – 4.60 (m, 2H), 2.47 (s, 3H), 2.34 (s, 3H), 2.33 (s, 3H), 2.09 (s, 3H), 1.70 (d, J = 6.8 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 148.1 (d, J = 8.0 Hz), 147.2 (d, J = 2.5 Hz), 143.6, 133.4 (d, J = 1.3 Hz), 132.7 (d, J = 1.3 Hz), 131.4 (d, J = 3.7 Hz), 131.2 (d, J = 1.3 Hz), 131.0, 130.4 (d, J = 2.0 Hz), 130.2 (d, J = 2.7 Hz), 129.4, 128.3, 128.2, 128.1, 127.8, 126.7, 52.6 (d, J = 12.0 Hz), 21.0 (d, J = 6.1 Hz), 17.5, 16.5
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 142.1
IR (neat) νmax (cm⁻¹)	2363, 2339, 1215, 1122, 852, 837, 758, 694, 590
HRMS (ESI)	m/z calcd. for C₃₂H₃₅NO₂P⁺ [M + H]⁺ 496.2400, found 496.2410
Optical rotation	[α]D20 = -228° (c = 1.0, CHCl3)

N,N-bis((S)-1-(naphthalen-2-yl)ethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.69 (d, J = 7.3 Hz, 2H), 7.56 – 7.27 (m, 17H), 7.23 (t, J = 7.4 Hz, 2H), 7.15 (d, J = 8.0 Hz, 1H), 4.84 – 4.72 (m, 2H), 1.88 (d, J = 7.1 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 152.0 (d, J = 8.4 Hz), 151.2 (d, J = 2.6 Hz), 140.5, 133.1, 132.5, 131.3 (d, J = 3.7 Hz), 130.2, 130.0, 129.3, 129.1, 128.4, 128.0, 127.5 (d, J = 4.3 Hz), 127.2 (d, J = 3.1 Hz), 126.2 (d, J = 2.1 Hz), 125.8, 125.7, 125.6, 124.8, 124.2, 122.7 (d, J = 1.6 Hz), 122.2, 52.9 (d, J = 11.7 Hz), 22.3 (d, J = 10.2 Hz)
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 146.1
IR (neat) νmax (cm⁻¹)	1433, 1246, 1117, 1097, 881, 816, 771, 744, 731, 694, 472
HRMS (ESI)	m/z calcd. for C₃₆H₃₁NO₂P⁺ [M + H]⁺ 540.2087, found 540.2097
Optical rotation	[α]D20 = -394° (c = 1.0, CHCl3)

(11bR)-N,N-bis((S)-1-(naphthalen-2-yl)ethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
¹H NMR (500 MHz, CDCl₃)	δ 8.00 – 7.19 (m, 26H), 4.77 – 4.63 (m, 2H), 1.87 (d, J = 6.9 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 150.2 (d, J = 7.3 Hz), 149.7, 143.3, 140.4, 133.6, 133.02, 132.96, 132.89, 132.5, 131.6, 130.6, 130.5, 129.6, 128.5, 128.4, 128.3, 128.0, 127.9, 127.8, 127.4, 127.34, 127.26, 126.17, 126.15, 126.11, 126.09, 125.8, 125.7, 125.6, 125.0, 124.9, 124.6, 124.2 (d, J = 5.3 Hz), 122.6, 122.5 (d, J = 1.9 Hz), 121.9 (d, J = 2.3 Hz), 52.6 (d, J = 12.3 Hz), 22.2
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 145.0
IR (neat) νmax (cm⁻¹)	1229, 943, 924, 818, 779, 744, 694, 625, 553, 474
HRMS (ESI)	m/z calcd. for C₄₄H₃₅NO₂P⁺ [M + H]⁺ 640.2400, found 640.2408
Optical rotation	[α]D20 = -506° (c = 1.0, CHCl3)

(11bS)-N,N-bis((S)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
¹H NMR (500 MHz, CDCl₃)	δ 8.00 (d, J = 8.8 Hz, 1H), 7.92 (d, J = 8.2 Hz, 1H), 7.81 (d, J = 8.7 Hz, 1H), 7.73 (d, J = 8.8 Hz, 1H), 7.57 (d, J = 9.3 Hz, 1H), 7.43 – 7.38 (m, 1H), 7.38 – 7.32 (m, 3H), 7.29 – 7.13 (m, 13H), 4.45 – 4.37 (m, 2H), 1.68 (d, J = 7.1 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 150.6 (d, J = 10.2 Hz), 149.9, 143.2, 133.0 (d, J = 15.9 Hz), 131.5, 130.6, 130.5, 129.7, 128.4, 128.2, 128.1 (d, J = 3.2 Hz), 127.9, 127.4, 127.3, 126.8, 126.2, 126.0, 124.9, 124.5, 124.3 (d, J = 5.6 Hz), 122.7, 122.55, 122.53, 121.3 (d, J = 2.7 Hz), 54.7 (d, J = 10.7 Hz), 23.2 (d, J = 11.9 Hz)
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 150.5
IR (neat) νmax (cm⁻¹)	1229, 1068, 947, 924, 818, 800, 783, 744, 694, 625, 557, 523
HRMS (ESI)	m/z calcd. for C₃₆H₃₁NO₂P⁺ [M + H]⁺ 540.2092, found 540.2104
Optical rotation	[α]D20 = +201° (c = 1.0, CHCl3)

N,N-bis((R)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.50 – 7.46 (m, 2H), 7.38 – 7.19 (m, 6H), 7.17 – 7.09 (m, 10H), 4.65 – 4.54 (m, 2H), 1.74 (d, J = 7.1 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 152.1 (d, J = 8.4 Hz), 151.2 (d, J = 2.6 Hz), 143.1, 131.4 (d, J = 3.8 Hz), 130.1, 130.0, 129.3, 129.1, 128.09, 128.07, 127.9, 126.8, 124.8, 124.1, 122.7 (d, J = 1.6 Hz), 122.2, 52.8 (d, J = 11.7 Hz), 22.4 (d, J = 9.7 Hz)
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 146.3
IR (neat) νmax (cm⁻¹)	889, 845, 754, 741, 735, 694, 671, 513
HRMS (ESI)	m/z calcd. for C₂₈H₂₇NO₂P⁺ [M + H]⁺ 440.1774, found 440.1784
Optical rotation	[α]D20 = +220° (c = 1.0, CHCl3)

1,2,4,8,10,11-hexamethyl-N,N-bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.23 – 6.86 (m, 12H), 4.56 – 4.45 (m, 2H), 2.41 (s, 3H), 2.23 (d, J = 7.2 Hz, 6H), 1.99 (s, 3H), 1.86 (s, 3H), 1.66 (d, J = 6.9 Hz, 6H), 1.58 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 147.9, 147.2 (d, J = 7.3 Hz), 143.7, 134.6 (d, J = 1.9 Hz), 133.8, 132.7 (d, J = 1.6 Hz), 131.3, 131.2, 131.1, 130.7 (d, J = 4.6 Hz), 128.9 (d, J = 1.9 Hz), 128.4 (d, J = 2.4 Hz), 128.0, 126.9, 126.6 (d, J = 2.9 Hz), 54.6 (d, J = 11.1 Hz), 23.2 (d, J = 11.6 Hz), 20.3, 20.2, 17.5, 17.0, 16.34, 16.31 (d, J = 2.5 Hz)
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 139.8
IR (neat) νmax (cm⁻¹)	1452, 1240, 922, 866, 779, 698, 617, 596, 548, 521
HRMS (ESI)	m/z calcd. for C₃₄H₃₉NO₂P⁺ [M + H]⁺ 524.2713, found 524.2722
Optical rotation	[α]D20 = -176° (c = 0.1, CHCl3)

N,N-bis((R)-1-phenylpropyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.50 (dt, J = 7.6, 1.9 Hz, 2H), 7.40 – 7.33 (m, 2H), 7.30 – 7.16 (m, 4H), 7.06 – 6.96 (m, 10H), 4.31 – 4.20 (m, 2H), 2.32 – 2.19 (m, 2H), 2.19 – 2.05 (m, 2H), 0.81 (t, J = 7.3 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 152.1 (d, J = 9.8 Hz), 151.1, 141.2, 131.7 (d, J = 4.0 Hz), 130.2, 130.0, 129.3, 129.2, 128.5 (d, J = 3.1 Hz), 127.7, 126.5, 124.9, 123.9, 122.7 (d, J = 2.0 Hz), 122.0, 60.0 (d, J = 9.5 Hz), 29.9, 28.5, 11.8
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 143.7
IR (neat) νmax (cm⁻¹)	1433, 1246, 1190, 881, 845, 756, 741, 694, 673
HRMS (ESI)	m/z calcd. for C₃₀H₃₁NO₂P⁺ [M + H]⁺ 468.2086, found 468.2090
Optical rotation	[α]D20 = +224° (c = 1.0, CHCl3)

(11bR)-N,N-bis((R)-1-phenylpropyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
¹H NMR (500 MHz, CDCl₃)	δ 8.01 (d, J = 8.7 Hz, 1H), 7.93 (d, J = 8.2 Hz, 1H), 7.85 (d, J = 7.8 Hz, 1H), 7.80 (d, J = 8.8 Hz, 1H), 7.58 (d, J = 8.7 Hz, 1H), 7.45 – 7.34 (m, 3H), 7.26 – 7.15 (m, 4H), 7.15 – 7.07 (m, 6H), 6.98 (dd, J = 6.3, 2.8 Hz, 4H), 4.21 – 4.10 (m, 2H), 2.21 – 2.03 (m, 4H), 0.76 (t, J = 7.3 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 150.6 (d, J = 9.3 Hz), 149.8, 141.5, 133.0 (d, J = 15.9 Hz), 131.5, 130.52, 130.48, 129.6, 128.8 (d, J = 2.7 Hz), 128.4, 128.2, 127.8, 127.31, 127.29, 126.7, 126.1, 126.0, 124.9, 124.5, 124.4 (d, J = 5.6 Hz), 122.9, 122.5, 122.4, 121.5 (d, J = 2.6 Hz), 61.4 (d, J = 8.6 Hz), 28.8 (d, J = 12.9 Hz), 12.1
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 149.1
IR (neat) νmax (cm⁻¹)	1229, 945, 818, 744, 694, 679, 625, 548, 523
HRMS (ESI)	m/z calcd. for C₃₈H₃₅NO₂P⁺ [M + H]⁺ 568.2400, found 568.2417
Optical rotation	[α]D20 = -176° (c = 1.0, CHCl3)

(2R)-1-((11bR)-2,6-diphenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline
¹H NMR (500 MHz, CDCl₃)	δ 8.14 (s, 1H), 8.10 (s, 1H), 8.03 (t, J = 7.6 Hz, 2H), 7.79 (d, J = 7.0 Hz, 2H), 7.73 (d, J = 7.0 Hz, 2H), 7.55 – 7.47 (m, 5H), 7.47 – 7.43 (m, 1H), 7.38 (d, J = 8.7 Hz, 1H), 7.35 – 7.24 (m, 5H), 6.89 (dd, J = 7.5, 1.6 Hz, 1H), 6.77 (td, J = 7.4, 1.2 Hz, 1H), 6.71 (td, J = 7.7, 1.7 Hz, 1H), 6.48 (ddd, J = 8.1, 3.0, 1.2 Hz, 1H), 3.77 – 3.69 (m, 1H), 2.44 (ddd, J = 16.5, 10.5, 6.1 Hz, 1H), 2.07 (dt, J = 16.2, 5.4 Hz, 1H), 1.31 (ddd, J = 10.4, 7.5, 5.3 Hz, 1H), 1.17 – 1.10 (m, 1H), 0.80 (d, J = 6.6 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 148.2 (d, J = 8.3 Hz), 147.1, 139.5 (d, J = 21.4 Hz), 137.8, 137.7, 135.2 (d, J = 2.5 Hz), 134.4, 132.8 (d, J = 1.8 Hz), 132.6 (d, J = 0.9 Hz), 131.5, 130.7, 130.6, 130.5, 130.3 (d, J = 1.4 Hz), 130.2, 128.8, 128.6, 128.4, 128.25, 128.17, 127.8 (d, J = 4.1 Hz), 127.6, 127.4, 127.3, 127.2, 126.2, 126.1, 126.0 (d, J = 1.7 Hz), 125.6 (d, J = 6.2 Hz), 125.4, 125.0, 123.2 (d, J = 2.6 Hz), 121.3 (d, J = 1.4 Hz), 119.6 (d, J = 31.0 Hz), 47.1 (d, J = 3.2 Hz), 28.9, 23.3, 20.4
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 139.6
IR (neat) νmax (cm⁻¹)	957, 946, 837, 748, 723, 696, 648, 632
HRMS (ESI)	m/z calcd. for C₄₂H₃₃NO₂P⁺ [M + H]⁺ 614.2243, found 614.2245
Optical rotation	[α]D20 = -320° (c = 1.5, CHCl3)

(2S)-1-((11bR)-2,6-diphenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline
¹H NMR (500 MHz, CDCl₃)	δ 8.11 (s, 1H), 8.04 – 8.01 (m, 1H), 7.98 (dd, J = 7.8, 1.6 Hz, 1H), 7.94 (s, 1H), 7.79 – 7.75 (m, 2H), 7.57 – 7.54 (m, 2H), 7.53 – 7.50 (m, 3H), 7.45 (dd, J = 8.3, 6.8 Hz, 2H), 7.41 – 7.32 (m, 7H), 6.94 (dd, J = 7.6, 1.5 Hz, 1H), 6.80 (td, J = 7.4, 1.2 Hz, 1H), 6.50 (td, J = 7.7, 1.6 Hz, 1H), 6.37 (d, J = 8.1 Hz, 1H), 4.16 – 4.06 (m, 1H), 2.66 (dt, J = 18.4, 9.6 Hz, 1H), 2.48 (dt, J = 17.0, 4.5 Hz, 1H), 1.48 – 1.41 (m, 2H), 0.60 (d, J = 6.8 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 147.3 (d, J = 4.7 Hz), 146.8 (d, J = 1.3 Hz), 139.5 (d, J = 18.4 Hz), 137.78, 137.76, 135.0, 134.9 (d, J = 1.7 Hz), 132.7 (d, J = 1.1 Hz), 132.5 (d, J = 0.9 Hz), 131.4, 130.9, 130.7, 130.4, 130.1 (d, J = 2.1 Hz), 130.0, 128.8, 128.6, 128.5, 128.2, 128.0, 127.6, 127.3, 127.2 (d, J = 3.2 Hz), 127.1, 126.9, 126.2, 126.1, 125.8, 125.4, 125.3 (d, J = 5.3 Hz), 125.0, 124.0 (d, J = 2.3 Hz), 121.9, 121.1 (d, J = 18.1 Hz), 46.1 (d, J = 12.0 Hz), 29.0, 22.7, 17.7
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 142.9
IR (neat) νmax (cm⁻¹)	960, 947, 839, 748, 725, 696, 648, 635, 600, 419, 404
HRMS (ESI)	m/z calcd. for C₄₂H₃₃NO₂P⁺ [M + H]⁺ 614.2243, found 614.2238
Optical rotation	[α]D20 = -100° (c = 1.5, CHCl3)

(2S)-1-((11bR)-2,6-bis(trimethylsilyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline
¹H NMR (500 MHz, CDCl₃)	δ 8.04 (s, 1H), 7.96 (s, 1H), 7.86 – 7.83 (m, 2H), 7.59 (s, 1H), 7.36 – 7.29 (m, 2H), 7.21 – 7.17 (m, 2H), 7.12 – 7.08 (m, 1H), 7.01 – 6.95 (m, 3H), 6.79 (td, J = 7.3, 1.1 Hz, 1H), 3.51 (s, 1H), 2.72 – 2.64 (m, 1H), 2.58 (dd, J = 17.2, 6.7 Hz, 1H), 1.54 – 1.49 (m, 1H), 1.10 – 1.03 (m, 1H), 0.85 (d, J = 6.7 Hz, 3H), 0.44 (s, 9H), 0.13 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 153.7, 153.1 (d, J = 5.1 Hz), 140.8, 137.9, 137.3, 136.7, 134.1 (d, J = 0.9 Hz), 134.0, 132.8 (d, J = 2.0 Hz), 132.4, 131.1, 130.5, 130.4, 128.5, 128.4, 127.0, 126.8, 126.5, 126.4, 125.2 (d, J = 4.4 Hz), 124.8, 124.5, 122.9 (d, J = 4.9 Hz), 121.5 (d, J = 2.6 Hz), 120.9 (d, J = 2.8 Hz), 118.5 (d, J = 40.0 Hz), 45.7, 26.5, 22.4, 0.3, 0.3, 0.1
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 140.8
IR (neat) νmax (cm⁻¹)	1219, 1009, 974, 945, 837, 822, 795, 743, 631, 590
HRMS (ESI)	m/z calcd. for C₃₆H₄₁NO₂PSi₂⁺ [M + H]⁺ 606.2408, found 606.2406
Optical rotation	[α]D20 = -293° (c = 1.1, CHCl3)

(2R)-1-((11bR)-2,6-bis(trimethylsilyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline
¹H NMR (500 MHz, CDCl₃)	δ 8.12 – 8.09 (m, 2H), 7.98 – 7.93 (m, 2H), 7.46 (ddd, J = 8.1, 5.8, 2.1 Hz, 1H), 7.42 (ddd, J = 8.0, 6.7, 1.2 Hz, 1H), 7.36 – 7.29 (m, 3H), 7.22 (ddd, J = 8.2, 6.8, 1.3 Hz, 1H), 7.18 – 7.07 (m, 3H), 6.99 (t, J = 7.5 Hz, 1H), 3.99 – 3.86 (m, 1H), 2.86 – 2.72 (m, 2H), 1.92 (tdd, J = 12.7, 7.0, 4.1 Hz, 1H), 1.52 – 1.48 (m, 1H), 0.71 (d, J = 6.6 Hz, 3H), 0.43 (s, 9H), 0.40 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 153.29, 153.27, 139.9 (d, J = 28.3 Hz), 137.2, 136.7, 134.2 (d, J = 0.9 Hz), 134.0 (d, J = 0.9 Hz), 132.7 (d, J = 1.9 Hz), 132.6, 131.1, 130.5, 129.7, 128.5, 128.4, 127.1, 126.9, 126.5, 126.4, 126.3, 126.2, 124.7, 124.5, 123.0 (d, J = 5.0 Hz), 121.7, 121.6, 121.4 (d, J = 29.8 Hz), 45.1, 28.4, 22.3, 0.6, 0.2, 0.2
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 142.2
IR (neat) νmax (cm⁻¹)	3841, 2968, 2957, 2941, 2924, 2897, 2370, 2351, 2328, 2316, 2307, 943, 781, 683, 636
HRMS (ESI)	m/z calcd. for C₃₆H₄₁NO₂PSi₂⁺ [M + H]⁺ 606.2408, found 606.2414
Optical rotation	[α]D20 = -226° (c = 1.6, CHCl3)

(2R)-1-((11bR)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline
¹H NMR (500 MHz, CDCl₃)	δ 8.02 (d, J = 8.8 Hz, 1H), 7.96 – 7.90 (m, 3H), 7.60 (d, J = 8.7 Hz, 1H), 7.54 (dd, J = 8.1, 2.9 Hz, 1H), 7.47 – 7.39 (m, 4H), 7.32 – 7.22 (m, 3H), 7.13 – 7.05 (m, 2H), 6.92 (t, J = 7.8 Hz, 1H), 3.77 – 3.67 (m, 1H), 2.86 – 2.75 (m, 2H), 2.05 – 1.93 (m, 1H), 1.47 – 1.38 (m, 1H), 0.95 (d, J = 6.6 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 150.1 (d, J = 7.3 Hz), 149.6, 139.9 (d, J = 24.2 Hz), 132.94 (d, J = 1.7 Hz), 132.86 (d, J = 1.1 Hz), 131.7, 130.8, 130.7, 130.1, 130.0, 128.5, 128.4, 127.3, 127.2, 126.53 (d, J = 2.4 Hz), 126.47 (d, J = 4.7 Hz), 126.3, 126.2, 125.1, 124.8, 124.3 (d, J = 5.8 Hz), 122.3 (d, J = 1.8 Hz), 122.0, 121.5 (d, J = 2.5 Hz), 119.9, 119.6, 45.9, 28.1, 23.0, 19.2
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 140.0
IR (neat) νmax (cm⁻¹)	1223, 1201, 941, 931, 820, 800, 743, 681, 625, 555
HRMS (ESI)	m/z calcd. for C₃₀H₂₅NO₂P⁺ [M + H]⁺ 462.1617, found 462.1621
Optical rotation	[α]D20 = -230° (c = 1.0, CHCl3)

(2R)-1-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline
¹H NMR (500 MHz, CDCl₃)	δ 7.87 (d, J = 8.7 Hz, 1H), 7.83 (d, J = 8.3 Hz, 2H), 7.79 (d, J = 8.7 Hz, 1H), 7.39 (d, J = 8.7 Hz, 1H), 7.37 – 7.30 (m, 4H), 7.26 – 7.13 (m, 4H), 7.00 (dd, J = 7.5, 1.5 Hz, 1H), 6.96 (td, J = 7.7, 1.7 Hz, 1H), 6.88 (td, J = 7.5, 1.2 Hz, 1H), 3.79 (qt, J = 6.6, 3.3 Hz, 1H), 2.76 – 2.63 (m, 2H), 1.90 – 1.81 (m, 1H), 1.43 – 1.37 (m, 1H), 0.77 (d, J = 6.7 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 149.7 (d, J = 6.6 Hz), 149.2, 139.9 (d, J = 25.6 Hz), 133.0 (d, J = 1.5 Hz), 132.7 (d, J = 0.9 Hz), 131.6, 130.9, 130.6, 129.74, 129.70, 128.5, 128.4, 127.3 (d, J = 4.2 Hz), 127.20, 127.19, 126.4, 126.3, 126.1, 125.0, 124.7, 124.2 (d, J = 5.2 Hz), 122.42 (d, J = 1.2 Hz), 122.36, 122.3 (d, J = 2.4 Hz), 122.1 (d, J = 1.8 Hz), 121.5 (d, J = 25.4 Hz), 45.4, 28.5, 22.4, 17.9
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 142.8
IR (neat) νmax (cm⁻¹)	1225, 943, 820, 797, 781, 748, 681, 629, 559
HRMS (ESI)	m/z calcd. for C₃₀H₂₅NO₂P⁺ [M + H]⁺ 462.1617, found 462.1619
Optical rotation	[α]D20 = +204° (c = 1.1, CHCl3)

(11bS)-N,N-bis((R)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
¹H NMR (500 MHz, CDCl₃)	δ 7.94 (d, J = 8.8 Hz, 2H), 7.92 – 7.87 (m, 2H), 7.58 (d, J = 8.8 Hz, 1H), 7.44 – 7.36 (m, 4H), 7.29 – 7.20 (m, 3H), 7.15 – 7.06 (m, 10H), 4.56 – 4.42 (m, 2H), 1.72 (d, J = 7.1 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 150.2 (d, J = 7.4 Hz), 149.7, 143.0, 132.9 (d, J = 7.4 Hz), 131.5, 130.6, 130.4, 129.6, 128.4, 128.2, 128.1 (d, J = 2.3 Hz), 127.9, 127.3, 127.2, 126.8, 126.12, 126.09, 124.9, 124.6, 124.2 (d, J = 5.2 Hz), 122.6, 122.53, 122.52, 121.9 (d, J = 2.3 Hz), 52.4 (d, J = 12.2 Hz), 22.1
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 145.3
IR (neat) νmax (cm⁻¹)	1230, 947, 924, 820, 779, 744, 694, 685, 625, 553, 523
HRMS (ESI)	m/z calcd. for C₃₆H₃₁NO₂P⁺ [M + H]⁺ 540.2092, found 540.2094
Optical rotation	[α]D20 = +458° (c = 1.0, CHCl3)

(11bR)-N,N-bis((R)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
¹H NMR (500 MHz, CDCl₃)	δ 8.00 (d, J = 8.8 Hz, 1H), 7.92 (d, J = 8.2 Hz, 1H), 7.81 (d, J = 8.7 Hz, 1H), 7.73 (d, J = 8.8 Hz, 1H), 7.57 (d, J = 9.3 Hz, 1H), 7.43 – 7.38 (m, 1H), 7.38 – 7.32 (m, 3H), 7.29 – 7.13 (m, 13H), 4.45 – 4.37 (m, 2H), 1.68 (d, J = 7.1 Hz, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 150.6 (d, J = 10.2 Hz), 149.9, 143.2, 133.0 (d, J = 15.9 Hz), 131.5, 130.6, 130.5, 129.7, 128.4, 128.2, 128.1 (d, J = 3.2 Hz), 127.9, 127.4, 127.3, 126.8, 126.2, 126.0, 124.9, 124.5, 124.3 (d, J = 5.6 Hz), 122.7, 122.55, 122.53, 121.3 (d, J = 2.7 Hz), 54.7 (d, J = 10.7 Hz), 23.2 (d, J = 11.9 Hz)
³¹P NMR {¹H} (202 MHz, CDCl₃)	δ 150.5
IR (neat) νmax (cm⁻¹)	1229, 945, 924, 818, 783, 744, 692, 677, 627, 523
HRMS (ESI)	m/z calcd. for C₃₆H₃₁NO₂P⁺ [M + H]⁺ 540.2092, found 540.2101
Optical rotation	[α]D20 = -198° (c = 1.0, CHCl3)

5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.87 (p, J = 1.4 Hz, 1H), 5.78 – 5.71 (m, 1H), 5.65 – 5.57 (m, 1H), 4.50 (dd, J = 6.3, 0.8 Hz, 2H), 2.38 – 2.25 (m, 8H), 2.06 (s, 3H), 2.02 – 1.96 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 170.9, 165.1, 134.3, 126.1, 125.3, 65.0, 37.5, 37.2, 29.9, 29.7, 22.8, 21.1
IR (neat) νmax (cm⁻¹)	1734, 1664, 1624, 1373, 1364, 1225, 1192, 1024, 964, 887, 490, 451
HRMS (ESI)	m/z calcd. for C₁₃H₁₉O₃⁺ [M + H]⁺ 223.1329, found 223.1326

1-(methylthio)-7-(3-oxocyclohex-1-en-1-yl)hept-4-en-3-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.86 – 5.85 (m, 1H), 5.77 – 5.67 (m, 1H), 5.49 – 5.40 (m, 1H), 5.30 – 5.25 (m, 1H), 2.48 – 2.44 (m, 2H), 2.37 – 2.33 (m, 2H), 2.32 – 2.21 (m, 6H), 2.09 (s, 3H), 2.04 (s, 3H), 2.01 – 1.89 (m, 3H), 1.88 – 1.73 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 170.4, 165.1, 133.0, 129.1, 126.2, 73.5, 37.5, 37.3, 34.1, 29.9, 29.7, 22.8, 21.4, 15.7
IR (neat) νmax (cm⁻¹)	2361, 2341, 2251, 1732, 1664, 1369, 1236, 1022, 964, 631, 534, 498
HRMS (ESI)	m/z calcd. for C₁₆H₂₄O₃SNa⁺ [M + Na]⁺ 319.1338, found 319.1316

2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.69 – 7.62 (m, 8H), 7.46 – 7.36 (m, 12H), 5.90 – 5.86 (m, 1H), 5.79 – 5.74 (m, 1H), 5.67 (t, J = 7.3 Hz, 1H), 5.50 (t, J = 7.1 Hz, 1H), 4.67 (s, 2H), 4.62 (s, 2H), 4.22 (s, 2H), 4.18 – 4.15 (m, 2H), 2.40 – 2.25 (m, 10H), 2.19 – 1.89 (m, 16H), 1.05 (s, 9H), 1.04 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.79, 199.76, 171.0, 170.9, 165.1, 165.0, 135.72, 135.67, 134.8, 134.3, 133.6, 133.4, 129.9, 129.8, 129.4, 127.9, 127.8, 126.2, 126.0, 66.4, 65.8, 59.7, 59.6, 37.8, 37.6, 37.5, 37.4, 29.8, 29.7, 26.95, 26.89, 25.0, 24.9, 22.82, 22.77, 21.2, 21.0, 19.41, 19.36
IR (neat) νmax (cm⁻¹)	1738, 1668, 1427, 1229, 1109, 1051, 1024, 822, 741, 700, 609, 503, 486
HRMS (ESI)	m/z calcd. for C₃₀H₃₉O₄Si⁺ [M + H]⁺ 491.2612, found 491.2620

2-methyl-5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.87 (s, 1H), 5.44 – 5.39 (m, 1H), 4.44 (s, 2H), 2.38 – 2.33 (m, 2H), 2.31 – 2.22 (m, 6H), 2.06 (s, 3H), 2.02 – 1.95 (m, 2H), 1.66 – 1.65 (m, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 171.0, 165.5, 131.6, 127.7, 126.0, 69.9, 37.50, 37.47, 29.9, 25.3, 22.8, 21.1, 14.2
IR (neat) νmax (cm⁻¹)	1734, 1663, 1649, 1369, 1230, 1192, 1022, 966, 887, 606, 509, 453
HRMS (ESI)	m/z calcd. for C₁₄H₂₁O₃⁺ [M + H]⁺ 237.1485, found 237.1488

E-1-(furan-2-yl)-5-(3-oxocyclohex-1-en-1-yl)pent-1-en-3-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.35 (d, J = 1.8 Hz, 1H), 6.42 (dd, J = 15.8, 1.0 Hz, 1H), 6.37 (dd, J = 3.3, 1.8 Hz, 1H), 6.27 (d, J = 3.3 Hz, 1H), 6.03 (dd, J = 15.8, 7.3 Hz, 1H), 5.87 (p, J = 1.5 Hz, 1H), 5.38 – 5.33 (m, 1H), 2.37 – 2.33 (m, 2H), 2.31 – 2.25 (m, 4H), 2.07 (s, 3H), 2.02 – 1.96 (m, 2H), 1.95 – 1.82 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.7, 170.4, 165.0, 151.7, 142.5, 126.0, 125.3, 121.5, 111.6, 109.4, 73.8, 37.4, 33.6, 31.7, 29.9, 22.8, 21.4
IR (neat) νmax (cm⁻¹)	2359, 2341, 2251, 1732, 1664, 1371, 1230, 1192, 1013, 960, 883, 739, 594, 530
HRMS (ESI)	m/z calcd. for C₁₇H₂₀O₄Na⁺ [M + Na]⁺ 311.1254, found 311.1230

5-(3-oxocyclohex-1-en-1-yl)-1-phenylpent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.38 – 7.27 (m, 5H), 6.20 (d, J = 5.2 Hz, 1H), 5.85 (p, J = 1.4 Hz, 1H), 5.73 – 5.65 (m, 2H), 2.35 – 2.25 (m, 6H), 2.25 – 2.21 (m, 2H), 2.09 (s, 3H), 1.98 – 1.89 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 170.1, 165.1, 139.5, 132.4, 129.9, 128.7, 128.2, 126.9, 126.3, 76.1, 37.4, 37.2, 29.8, 29.7, 22.7, 21.5
IR (neat) νmax (cm⁻¹)	1732, 1662, 1371, 1229, 1192, 1018, 962, 887, 756, 698
HRMS (ESI)	m/z calcd. for C₁₉H₂₃O₃⁺ [M + H]⁺ 299.1642, found 299.1640

E-1-(4-methoxyphenyl)-5-(3-oxocyclohex-1-en-1-yl)pent-1-en-3-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.33 – 7.30 (m, 2H), 6.87 – 6.83 (m, 2H), 6.57 (d, J = 15.9 Hz, 1H), 5.96 (dd, J = 15.9, 7.6 Hz, 1H), 5.89 (p, J = 1.4 Hz, 1H), 5.38 (dtd, J = 7.6, 6.5, 1.0 Hz, 1H), 3.81 (s, 3H), 2.38 – 2.33 (m, 2H), 2.32 – 2.25 (m, 4H), 2.07 (s, 3H), 2.02 – 1.92 (m, 3H), 1.90 – 1.83 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 170.4, 165.1, 159.8, 133.1, 128.9, 128.0, 126.0, 124.5, 114.2, 74.5, 55.5, 37.5, 33.8, 31.9, 29.9, 22.8, 21.5
IR (neat) νmax (cm⁻¹)	1736, 1664, 1607, 1510, 1371, 1234, 1175, 1024, 964, 633, 496
HRMS (ESI)	m/z calcd. for C₂₀H₂₄O₄Na⁺ [M + Na]⁺ 351.1567, found 351.1568

1-(4-fluorophenyl)-5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.30 – 7.26 (m, 2H), 7.05 – 7.00 (m, 2H), 6.18 (d, J = 5.4 Hz, 1H), 5.85 (p, J = 1.3 Hz, 1H), 5.72 – 5.61 (m, 2H), 2.34 – 2.26 (m, 6H), 2.26 – 2.22 (m, 2H), 2.08 (s, 3H), 1.97 – 1.91 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 170.0, 165.0, 162.5 (d, J = 246.7 Hz), 135.4 (d, J = 3.2 Hz), 132.6, 129.6, 128.8 (d, J = 8.2 Hz), 126.3, 115.6 (d, J = 21.6 Hz), 75.4, 37.4, 37.2, 29.8, 29.6, 22.7, 21.4
¹⁹F NMR {¹H} (471 MHz, CDCl₃)	-114.0
IR (neat) νmax (cm⁻¹)	1736, 1663, 1508, 1371, 1221, 1016, 964, 835, 627, 548, 525, 496
HRMS (ESI)	m/z calcd. for C₁₉H₂₂FO₃⁺ [M + H]⁺ 317.1547, found 317.1546

1-(4-chlorophenyl)-5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.34 – 7.29 (m, 2H), 7.26 – 7.22 (m, 2H), 6.16 (d, J = 6.2 Hz, 1H), 5.84 (p, J = 1.4 Hz, 1H), 5.72 – 5.60 (m, 2H), 2.34 – 2.26 (m, 6H), 2.25 – 2.22 (m, 2H), 2.08 (s, 3H), 1.97 – 1.91 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 170.0, 165.0, 138.0, 134.0, 132.9, 129.4, 128.9, 128.4, 126.3, 75.3, 37.4, 37.1, 29.8, 29.6, 22.7, 21.4
IR (neat) νmax (cm⁻¹)	1736, 1663, 1369, 1227, 1090, 1013, 964, 820, 635, 606, 538, 501
HRMS (ESI)	m/z calcd. for C₁₉H₂₁ClO₃Na⁺ [M + Na]⁺ 355.1071, found 355.1077

E-1-(3-chlorophenyl)-5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.31 – 7.25 (m, 3H), 7.20 – 7.15 (m, 1H), 6.15 (d, J = 6.6 Hz, 1H), 5.85 (p, J = 1.4 Hz, 1H), 5.75 – 5.68 (m, 1H), 5.66 – 5.59 (m, 1H), 2.35 – 2.27 (m, 6H), 2.26 – 2.22 (m, 2H), 2.10 (s, 3H), 1.98 – 1.91 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 170.0, 165.0, 141.6, 134.6, 133.2, 130.0, 129.2, 128.3, 126.9, 126.3, 125.1, 75.3, 37.4, 37.1, 29.8, 29.7, 22.7, 21.4
IR (neat) νmax (cm⁻¹)	1736, 1664, 1371, 1227, 1194, 964, 887, 787, 694, 633, 501, 457
HRMS (ESI)	m/z calcd. for C₁₉H₂₁ClO₃Na⁺ [M + H]⁺ 355.1071, found 355.1075

E-1-(2-chlorophenyl)-5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.41 (dd, J = 7.7, 1.7 Hz, 1H), 7.35 (dd, J = 7.8, 1.3 Hz, 1H), 7.27 (td, J = 7.6, 1.4 Hz, 1H), 7.22 (td, J = 7.6, 1.8 Hz, 1H), 6.55 (d, J = 6.2 Hz, 1H), 5.82 (p, J = 1.4 Hz, 1H), 5.73 – 5.66 (m, 1H), 5.65 – 5.59 (m, 1H), 2.32 – 2.25 (m, 6H), 2.24 – 2.20 (m, 2H), 2.10 (s, 3H), 1.95 – 1.88 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 169.7, 165.1, 137.3, 133.0, 132.7, 129.8, 129.2, 128.1, 127.8, 127.2, 126.3, 72.7, 37.4, 37.2, 29.8, 29.7, 22.7, 21.3
IR (neat) νmax (cm⁻¹)	1736, 1664, 1371, 1229, 1192, 1018, 964, 758, 631, 532, 498
HRMS (ESI)	m/z calcd. for C₁₉H₂₁ClO₃Na⁺ [M + H]⁺ 355.1071, found 355.1079

6-(3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.87 (p, J = 1.4 Hz, 1H), 5.78 – 5.54 (m, 2H), 4.51 (dd, J = 6.4, 0.8 Hz, 2H), 2.38 – 2.33 (m, 2H), 2.29 – 2.25 (m, 2H), 2.24 – 2.19 (m, 2H), 2.17 – 2.04 (m, 5H), 2.02 – 1.95 (m, 2H), 1.65 – 1.57 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 171.0, 166.0, 135.2, 126.0, 125.0, 65.2, 37.5, 31.8, 29.8, 26.2, 22.9, 21.2
IR (neat) νmax (cm⁻¹)	1736, 1662, 1624, 1364, 1227, 1192, 1024, 964, 887
HRMS (ESI)	m/z calcd. for C₁₄H₂₁O₃⁺ [M + H]⁺ 237.1485, found 237.1488

1-(methylthio)-8-(3-oxocyclohex-1-en-1-yl)oct-4-en-3-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.86 (p, J = 1.4 Hz, 1H), 5.71 (dtd, J = 15.3, 6.8, 0.9 Hz, 1H), 5.40 (ddt, J = 15.4, 7.4, 1.5 Hz, 1H), 5.31 – 5.26 (m, 1H), 2.49 – 2.45 (m, 2H), 2.35 (dd, J = 7.4, 6.0 Hz, 2H), 2.29 – 2.17 (m, 4H), 2.10 (s, 3H), 2.09 – 2.05 (m, 2H), 2.05 (s, 3H), 2.01 – 1.91 (m, 3H), 1.87 – 1.72 (m, 1H), 1.62 – 1.55 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 170.4, 166.0, 133.9, 128.7, 126.0, 73.7, 37.48, 37.47, 34.2, 31.8, 30.0, 29.8, 26.2, 22.9, 21.5, 15.7
IR (neat) νmax (cm⁻¹)	2922, 1734, 1666, 1624, 1373, 1238, 1020, 964, 800, 629, 534, 496
HRMS (ESI)	m/z calcd. for C₁₇H₂₇O₃S⁺ [M + H]⁺ 311.1675, found 311.1650

2-methyl-6-(3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.87 (s, 1H), 5.44 (t, J = 7.2 Hz, 1H), 4.45 (s, 2H), 2.39 – 2.33 (m, 2H), 2.30 – 2.18 (m, 4H), 2.13 – 2.04 (m, 5H), 1.99 (p, J = 6.3 Hz, 2H), 1.64 (s, 3H), 1.62 – 1.54 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.0, 171.1, 166.2, 131.1, 128.7, 126.0, 70.2, 37.7, 37.5, 29.8, 27.3, 26.6, 22.9, 21.2, 14.2
IR (neat) νmax (cm⁻¹)	2359, 2341, 2258, 1736, 1659, 1427, 1377, 1230, 1022, 995
HRMS (ESI)	m/z calcd. for C₁₅H₂₃O₃⁺ [M + H]⁺ 251.1642, found 251.1644

E-1-(furan-2-yl)-6-(3-oxocyclohex-1-en-1-yl)hex-1-en-3-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.34 (d, J = 1.8 Hz, 1H), 6.40 (dd, J = 15.9, 1.0 Hz, 1H), 6.36 (dd, J = 3.3, 1.8 Hz, 1H), 6.26 (d, J = 3.2 Hz, 1H), 6.03 (dd, J = 15.8, 7.3 Hz, 1H), 5.86 (p, J = 1.4 Hz, 1H), 5.36 (dtd, J = 7.1, 6.0, 1.1 Hz, 1H), 2.37 – 2.33 (m, 2H), 2.28 – 2.21 (m, 4H), 2.07 (s, 3H), 2.02 – 1.93 (m, 2H), 1.78 – 1.62 (m, 2H), 1.61 – 1.51 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 170.4, 165.6, 151.9, 142.4, 126.0, 125.8, 121.1, 111.5, 109.2, 74.0, 37.7, 37.4, 34.2, 29.7, 22.8, 22.6, 21.4
IR (neat) νmax (cm⁻¹)	1732, 1664, 1371, 1234, 1192, 1013, 962, 883, 737, 629, 594, 536, 496
HRMS (ESI)	m/z calcd. for C₁₈H₂₂O₄Na⁺ [M + Na]⁺ 325.1410, found 325.1378

6-(3-oxocyclohex-1-en-1-yl)-1-phenylhex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.39 – 7.27 (m, 5H), 6.22 (d, J = 6.2 Hz, 1H), 5.85 (p, J = 1.4 Hz, 1H), 5.77 – 5.53 (m, 2H), 2.37 – 2.31 (m, 2H), 2.27 – 2.23 (m, 2H), 2.22 – 2.16 (m, 2H), 2.10 (s, 3H), 2.09 – 2.06 (m, 2H), 2.00 – 1.94 (m, 2H), 1.65 – 1.55 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 170.2, 166.0, 139.7, 133.5, 129.4, 128.7, 128.1, 127.0, 126.0, 76.3, 37.49, 37.47, 31.8, 29.8, 26.2, 22.8, 21.5
IR (neat) νmax (cm⁻¹)	1734, 1664, 1371, 1230, 1018, 964, 729, 700, 631, 525, 496
HRMS (ESI)	m/z calcd. for C₂₀H₂₄O₃Na⁺ [M + Na]⁺ 335.1618, found 335.1632

E-1-(4-methoxyphenyl)-6-(3-oxocyclohex-1-en-1-yl)hex-1-en-3-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.33 – 7.29 (m, 2H), 6.87 – 6.82 (m, 2H), 6.55 (d, J = 15.9 Hz, 1H), 5.96 (dd, J = 15.9, 7.6 Hz, 1H), 5.88 – 5.86 (m, 1H), 5.41 – 5.35 (m, 1H), 3.80 (s, 3H), 2.37 – 2.33 (m, 2H), 2.29 – 2.21 (m, 4H), 2.07 (s, 3H), 2.01 – 1.95 (m, 2H), 1.80 – 1.62 (m, 2H), 1.61 – 1.51 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 170.5, 165.7, 159.7, 132.7, 129.0, 128.0, 126.1, 125.0, 114.1, 74.7, 55.4, 37.8, 37.5, 34.3, 29.7, 22.8, 22.7, 21.5
IR (neat) νmax (cm⁻¹)	2341, 2197, 2040, 1738, 1728, 1666, 1607, 1512, 1371, 1246, 1175, 1030, 964
HRMS (ESI)	m/z calcd. for C₂₁H₂₆O₄Na⁺ [M + Na]⁺ 365.1723, found 365.1728

1-(4-fluorophenyl)-6-(3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.34 – 7.28 (m, 2H), 7.08 – 6.99 (m, 2H), 6.19 (d, J = 6.1 Hz, 1H), 5.85 (p, J = 1.4 Hz, 1H), 5.73 – 5.60 (m, 2H), 2.37 – 2.33 (m, 2H), 2.26 (t, J = 6.0 Hz, 2H), 2.19 (t, J = 7.3 Hz, 2H), 2.09 (s, 3H), 2.08 – 2.04 (m, 2H), 2.01 – 1.94 (m, 2H), 1.63 – 1.56 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.0, 170.1, 166.0, 162.5 (d, J = 246.5 Hz), 135.5 (d, J = 3.1 Hz), 133.6, 129.2, 128.8 (d, J = 7.6 Hz), 126.0, 115.6 (d, J = 21.6 Hz), 75.6, 37.48, 37.47, 31.7, 29.8, 26.2, 22.8, 21.5
¹⁹F NMR {¹H} (471 MHz, CDCl₃)	-114.1
IR (neat) νmax (cm⁻¹)	1715, 1657, 1510, 1375, 1230, 1157, 1088, 1045, 879, 837, 457
HRMS (ESI)	m/z calcd. for C₂₀H₂₃FO₃Na⁺ [M + Na]⁺ 353.1523, found 353.1531

1-(4-chlorophenyl)-6-(3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.25 – 7.14 (m, 4H), 6.08 (d, J = 6.5 Hz, 1H), 5.76 (p, J = 1.4 Hz, 1H), 5.65 – 5.49 (m, 2H), 2.28 – 2.24 (m, 2H), 2.16 (t, J = 5.9 Hz, 2H), 2.10 (t, J = 7.6 Hz, 2H), 2.00 (s, 3H), 2.00 – 1.96 (m, 2H), 1.91 – 1.85 (m, 2H), 1.54 – 1.47 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 170.0, 165.9, 138.2, 133.9, 129.0, 128.8, 128.4, 126.0, 75.5, 37.4, 31.7, 29.8, 26.1, 22.8, 21.4
IR (neat) νmax (cm⁻¹)	2359, 1736, 1668, 1491, 1371, 1230, 1090, 1014, 964, 822
HRMS (ESI)	m/z calcd. for C₂₀H₂₃ClO₃Na⁺ [M + Na]⁺ 369.1228, found 369.1233

E-1-(3-chlorophenyl)-6-(3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.32 – 7.25 (m, 3H), 7.21 – 7.18 (m, 1H), 6.17 (d, J = 6.8 Hz, 1H), 5.85 (p, J = 1.4 Hz, 1H), 5.77 – 5.67 (m, 1H), 5.65 – 5.55 (m, 1H), 2.38 – 2.33 (m, 2H), 2.26 (t, J = 5.6 Hz, 2H), 2.19 (t, J = 7.8 Hz, 2H), 2.11 (s, 3H), 2.10 – 2.05 (m, 2H), 2.01 – 1.94 (m, 2H), 1.63 – 1.56 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 170.0, 165.9, 141.8, 134.5, 134.2, 130.0, 128.8, 128.2, 127.0, 126.0, 125.1, 75.5, 37.5, 31.7, 29.8, 26.1, 22.8, 21.4
IR (neat) νmax (cm⁻¹)	2930, 1738, 1666, 1425, 1369, 1229, 1194, 1020, 964, 887, 787, 694, 627, 528
HRMS (ESI)	m/z calcd. for C₂₀H₂₃ClO₃Na⁺ [M + Na]⁺ 369.1228, found 369.1233

1-(2-chlorophenyl)-6-(3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 7.44 (dd, J = 7.7, 1.8 Hz, 1H), 7.36 (dd, J = 7.9, 1.4 Hz, 1H), 7.28 (td, J = 7.5, 1.4 Hz, 1H), 7.23 (td, J = 7.6, 1.8 Hz, 1H), 6.56 (d, J = 6.6 Hz, 1H), 5.83 (p, J = 1.4 Hz, 1H), 5.74 – 5.66 (m, 1H), 5.63 – 5.54 (m, 1H), 2.36 – 2.32 (m, 2H), 2.24 (t, J = 5.7 Hz, 2H), 2.17 (t, J = 7.5 Hz, 2H), 2.11 (s, 3H), 2.09 – 2.04 (m, 2H), 2.01 – 1.91 (m, 2H), 1.58 (p, J = 7.5 Hz, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 169.8, 166.1, 137.4, 134.2, 132.7, 129.8, 129.1, 127.8, 127.7, 127.2, 126.0, 72.9, 37.5, 37.4, 31.7, 29.8, 26.2, 22.8, 21.3
IR (neat) νmax (cm⁻¹)	1736, 1659, 1375, 1230, 1082, 1043, 1024, 970, 881, 756, 486
HRMS (ESI)	m/z calcd. for C₂₀H₂₃ClO₃Na⁺ [M + Na]⁺ 369.1228, found 369.1229

E-8-(5-(3-oxocyclohex-1-en-1-yl)pent-1-en-1-yl)-1,4-dioxaspiro[4.5]decan-8-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.86 (p, J = 1.5 Hz, 1H), 5.75 (dt, J = 15.9, 1.4 Hz, 1H), 5.59 (dt, J = 15.9, 6.8 Hz, 1H), 3.98 – 3.91 (m, 4H), 2.37 – 2.33 (m, 2H), 2.31 – 2.25 (m, 4H), 2.19 (t, J = 7.7 Hz, 2H), 2.09 – 2.03 (m, 2H), 2.00 (s, 3H), 2.02 – 1.95 (m, 2H), 1.83 – 1.73 (m, 4H), 1.62 – 1.53 (m, 4H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.0, 170.1, 166.4, 133.7, 129.6, 125.9, 108.2, 80.5, 64.5, 64.4, 37.5, 37.4, 32.8, 31.9, 30.8, 29.8, 26.4, 22.9, 22.3
IR (neat) νmax (cm⁻¹)	2934, 1732, 1666, 1624, 1369, 1227, 1095, 1034, 968, 631, 532, 513, 496, 451
HRMS (ESI)	m/z calcd. for C₂₁H₃₀O₅Na⁺ [M + Na]⁺ 385.1985, found 385.1959

6-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.87 (p, J = 1.4 Hz, 1H), 5.79 – 5.53 (m, 2H), 4.51 (dd, J = 6.4, 0.9 Hz, 2H), 2.23 – 2.04 (m, 11H), 1.64 – 1.55 (m, 2H), 1.03 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 200.1, 171.0, 163.6, 135.2, 125.0, 65.2, 51.2, 44.1, 37.5, 33.8, 31.8, 28.4, 26.1, 21.2
IR (neat) νmax (cm⁻¹)	1736, 1664, 1628, 1367, 1227, 1024, 968, 903, 625, 523, 461
HRMS (ESI)	m/z calcd. for C₁₆H₂₅O₃⁺ [M + H]⁺ 265.1798, found 265.1803

6-(4,4-dimethyl-3-oxocyclohex-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.79 – 5.77 (m, 1H), 5.77 – 5.55 (m, 2H), 4.51 (dd, J = 6.4, 0.8 Hz, 2H), 2.47 – 2.40 (m, 2H), 2.23 – 2.16 (m, 2H), 2.12 (q, J = 6.9 Hz, 2H), 2.06 (s, 3H), 1.89 – 1.81 (m, 2H), 1.60 (p, J = 7.5 Hz, 2H), 1.16 (s, 6H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.6, 172.2, 171.0, 135.4, 124.9, 124.6, 65.2, 38.1, 35.8, 34.4, 32.0, 31.3, 26.7, 26.6, 21.2
IR (neat) νmax (cm⁻¹)	1736, 1664, 1555, 1427, 1367, 1227, 1194, 1041, 1024, 982, 889
HRMS (ESI)	m/z calcd. for C₁₆H₂₅O₃⁺ [M + H]⁺ 265.1798, found 265.1801

6-(3-oxocyclopent-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.98 – 5.91 (m, 1H), 5.81 – 5.55 (m, 2H), 4.51 (dd, J = 6.4, 0.8 Hz, 2H), 2.59 – 2.56 (m, 2H), 2.44 – 2.38 (m, 4H), 2.21 – 2.10 (m, 2H), 2.06 (s, 3H), 1.74 – 1.65 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 210.1, 182.5, 171.0, 135.0, 129.8, 125.1, 65.1, 35.4, 33.0, 31.9, 31.7, 26.3, 21.2
IR (neat) νmax (cm⁻¹)	1736, 1701, 1674, 1612, 1439, 1377, 1364, 1227, 1182, 1024, 968, 841, 629, 509
HRMS (ESI)	m/z calcd. for C₁₃H₁₉O₃⁺ [M + H]⁺ 223.1329, found 223.1331

6-(3-oxocyclohept-1-en-1-yl)hex-2-en-1-yl acetate
¹H NMR (500 MHz, CDCl₃)	δ 5.90 (s, 1H), 5.78 – 5.54 (m, 2H), 4.51 (dd, J = 6.4, 0.8 Hz, 2H), 2.59 – 2.54 (m, 2H), 2.43 – 2.37 (m, 2H), 2.22 – 2.17 (m, 2H), 2.16 – 2.03 (m, 5H), 1.83 – 1.75 (m, 4H), 1.62 – 1.55 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 204.2, 171.0, 161.7, 135.4, 129.6, 124.8, 65.2, 42.3, 40.5, 32.7, 31.8, 26.9, 25.3, 21.4, 21.2
IR (neat) νmax (cm⁻¹)	2363, 2341, 2330, 2251, 1736, 1657, 1452, 1364, 1225, 1024, 968, 631, 525, 498
HRMS (ESI)	m/z calcd. for C₁₅H₂₃O₃⁺ [M + H]⁺ 251.1642, found 251.1643

methyl (5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl) carbonate
¹H NMR (500 MHz, CDCl₃)	δ 5.86 (p, J = 1.4 Hz, 1H), 5.82 – 5.75 (m, 1H), 5.67 – 5.60 (m, 1H), 4.56 (dd, J = 6.4, 0.9 Hz, 2H), 3.78 (s, 3H), 2.38 – 2.34 (m, 2H), 2.34 – 2.25 (m, 6H), 2.02 – 1.95 (m, 2H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.8, 165.0, 155.7, 135.1, 126.2, 124.7, 68.3, 54.9, 37.5, 37.2, 29.9, 29.6, 22.8
IR (neat) νmax (cm⁻¹)	1743, 1662, 1623, 1442, 1251, 1192, 943, 887, 793
HRMS (ESI)	m/z calcd. for C₁₃H₁₉O₄⁺ [M + H]⁺ 239.1278, found 239.1277

tert-butyl (5-(3-oxocyclohex-1-en-1-yl)pent-2-en-1-yl) carbonate
¹H NMR (500 MHz, CDCl₃)	δ 5.88 – 5.84 (m, 1H), 5.80 – 5.73 (m, 1H), 5.67 – 5.58 (m, 1H), 4.49 (d, J = 6.4 Hz, 2H), 2.37 – 2.33 (m, 2H), 2.33 – 2.24 (m, 6H), 2.02 – 1.94 (m, 2H), 1.48 (s, 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 199.9, 165.2, 153.4, 134.6, 126.1, 125.1, 82.3, 67.4, 37.5, 37.2, 29.9, 29.7, 27.9, 22.8
IR (neat) νmax (cm⁻¹)	1736, 1666, 1369, 1273, 1250, 1155, 1113, 966, 856, 795
HRMS (ESI)	m/z calcd. for C₁₆H₂₅O₄⁺ [M + H]⁺ 281.1747, found 281.1754

(4aS,8R,8aS)-4a-methyl-8-vinyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 6.17 (ddd, J = 17.4, 10.2, 7.3 Hz, 1H), 5.01 – 4.81 (m, 2H), 2.44 – 2.34 (m, 2H), 2.32 – 2.19 (m, 2H), 1.90 – 1.79 (m, 3H), 1.75 – 1.68 (m, 1H), 1.64 – 1.39 (m, 5H), 1.18 (s, 3H), 1.05 (d, J = 13.2 Hz, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.2, 144.0, 112.9, 60.3, 43.4, 40.9, 40.6, 39.0, 31.9, 27.2, 26.7, 22.8, 21.5
IR (neat) νmax (cm⁻¹)	2928, 1707, 1088, 1047, 879, 631, 534, 521, 507, 492
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O⁺ [M + H]⁺ 193.1587, found 193.1588
Optical rotation	[α]D20 = -90° (c = 1.0, CHCl3, er = 84:16)
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 0 min]	For major diastereomer, er = 84:16 [t (major) = 33.7 min, t (minor) = 33.1 min]

(4aS,8S,8aS)-4a-methyl-8-vinyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 5.52 (ddd, J = 17.1, 10.2, 8.5 Hz, 1H), 4.99 – 4.85 (m, 2H), 2.46 (tdd, J = 12.0, 8.6, 3.7 Hz, 1H), 2.34 (td, J = 13.8, 7.3 Hz, 1H), 2.26 – 2.11 (m, 2H), 1.99 – 1.92 (m, 1H), 1.91 – 1.82 (m, 1H), 1.80 (d, 1H), 1.78 – 1.73 (m, 1H), 1.72 – 1.51 (m, 3H), 1.22 – 1.06 (m, 3H), 0.90 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.6, 141.0, 114.3, 64.9, 42.5, 39.3, 37.9, 37.6, 32.6, 29.5, 28.1, 22.5, 21.1
IR (neat) νmax (cm⁻¹)	2928, 2870, 1705, 1448, 1311, 1232, 912, 644, 505, 469
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O⁺ [M + H]⁺ 193.1587, found 193.1590
Optical rotation	[α]D20 = +66° (c = 1.0, CHCl3, er = 84:16)
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 5 min]	For minor diastereomer, er = 84:16 [t (major) = 48.0 min, t (minor) = 42.3 min]

(4aS,8R,8aR)-4a-methyl-8-vinyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 5.77 (ddd, J = 17.2, 10.5, 6.6 Hz, 1H), 4.97 (dt, J = 17.5, 1.5 Hz, 1H), 4.91 (dt, J = 10.6, 1.3 Hz, 1H), 2.40 – 2.30 (m, 2H), 2.29 – 2.24 (m, 1H), 2.22 (d, J = 11.2 Hz, 1H), 1.99 – 1.87 (m, 2H), 1.80 – 1.74 (m, 1H), 1.66 – 1.58 (m, 1H), 1.57 – 1.48 (m, 4H), 1.37 – 1.29 (m, 1H), 1.16 – 1.05 (m, 1H), 0.80 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.0, 142.9, 113.2, 62.5, 42.9, 41.2, 40.9 (2C), 35.0, 32.2, 23.8, 20.9, 17.5
IR (neat) νmax (cm⁻¹)	2934, 2849, 2262, 2021, 1981, 1713, 631, 550, 542, 525, 509, 492
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O⁺ [M + H]⁺ 193.1587, found 193.1585
Optical rotation	[α]D20 = +34° (c = 1.0, CHCl3, er = 84:16)

(4aS,8S,8aR)-8-acetyl-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 2.71 – 2.64 (m, 1H), 2.62 (dd, J = 11.0, 1.1 Hz, 1H), 2.31 (tdd, J = 13.2, 7.5, 1.1 Hz, 1H), 2.25 – 2.21 (m, 1H), 2.21 (s, 3H), 1.96 – 1.77 (m, 3H), 1.67 – 1.42 (m, 5H), 1.30 (td, J = 13.2, 4.5 Hz, 1H), 1.05 (qd, J = 12.8, 4.5 Hz, 1H), 0.73 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.3, 211.5, 59.3, 45.0, 41.1, 40.5, 39.8, 39.4, 29.7, 29.2, 22.5, 20.8, 17.5
IR (neat) νmax (cm⁻¹)	2930, 2868, 1705, 1425, 1381, 1352, 1311, 1267, 1215, 1169, 1090, 490
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O₂⁺ [M + H]⁺ 209.1536, found 209.1537
Optical rotation	[α]D20 = -22° (c = 1.0, CHCl3, er = 84:16)

(4aS,8S,8aR)-4a-methyl-8-(prop-1-en-2-yl)octahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 4.66 (p, J = 1.5 Hz, 1H), 4.56 – 4.54 (m, 1H), 2.51 (dd, J = 11.4, 1.1 Hz, 1H), 2.35 (tdd, J = 12.6, 7.5, 1.1 Hz, 1H), 2.26 (ddt, J = 12.5, 5.0, 1.9 Hz, 1H), 2.20 (td, J = 12.0, 3.9 Hz, 1H), 2.01 – 1.87 (m, 2H), 1.84 – 1.79 (m, 1H), 1.76 (s, 3H), 1.66 (td, J = 13.1, 5.3 Hz, 1H), 1.57 – 1.48 (m, 4H), 1.39 – 1.32 (m, 1H), 1.11 – 1.02 (m, 1H), 0.80 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.1, 150.9, 107.8, 61.5, 42.8, 41.4, 41.3, 41.0, 38.9, 33.8, 23.8, 22.5, 21.5, 17.5
IR (neat) νmax (cm⁻¹)	2922, 2849, 2359, 2341, 2257, 1713, 1441, 1383, 1184, 1088, 876
HRMS (ESI)	m/z calcd. for C₁₄H₂₃O⁺ [M + H]⁺ 207.1743, found 207.1743
Optical rotation	[α]D20 = +25° (c = 0.5, CHCl3, er = 84:16)

(4aS,8R,8aS)-8-acetyl-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 2.88 (td, J = 11.0, 3.9 Hz, 1H), 2.47 (ddd, J = 14.3, 12.3, 7.0 Hz, 1H), 2.28 (d, J = 10.8 Hz, 1H), 2.23 – 2.16 (m, 1H), 2.09 (s, 3H), 2.09 – 2.02 (m, 1H), 1.99 – 1.80 (m, 3H), 1.70 – 1.54 (m, 3H), 1.44 (dtd, J = 12.9, 11.2, 4.7 Hz, 1H), 1.27 – 1.17 (m, 2H), 0.94 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 213.2, 210.5, 60.2, 51.6, 38.4, 37.8, 37.6, 30.7, 28.0, 28.0, 27.2, 22.2, 20.4
IR (neat) νmax (cm⁻¹)	2930, 2870, 1697, 1450, 1429, 1358, 1234, 1200, 625, 575, 530, 507, 465
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O₂⁺ [M + H]⁺ 209.1536, found 209.1541
Optical rotation	[α]D20 = +53° (c = 1.0, CHCl3, er = 84:16)

(4aS,8R,8aS)-4a-methyl-8-(prop-1-en-2-yl)octahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 4.68 – 4.62 (m, 2H), 2.58 (td, J = 12.0, 3.1 Hz, 1H), 2.42 (td, J = 13.8, 7.3 Hz, 1H), 2.24 (td, J = 13.7, 4.9 Hz, 1H), 2.09 (ddq, J = 13.8, 4.9, 1.6 Hz, 1H), 2.04 (d, J = 11.9 Hz, 1H), 1.94 (dddt, J = 14.3, 7.2, 4.6, 2.1 Hz, 1H), 1.90 – 1.79 (m, 1H), 1.72 – 1.57 (m, 3H), 1.64 – 1.63 (m, 3H), 1.57 – 1.52 (m, 1H), 1.33 – 1.25 (m, 1H), 1.19 (td, J = 13.4, 4.6 Hz, 1H), 1.08 (dddd, J = 13.8, 5.9, 2.5, 1.4 Hz, 1H), 0.91 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.6, 147.1, 111.7, 62.5, 46.4, 39.5, 37.8, 37.3, 31.5, 29.4, 28.2, 22.5, 21.5, 17.7
IR (neat) νmax (cm⁻¹)	2924, 2872, 1705, 1645, 1448, 1375, 1306, 1232, 1200, 1049, 889, 554, 494
HRMS (ESI)	m/z calcd. for C₁₄H₂₃O⁺ [M + H]⁺ 207.1743, found 207.1748
Optical rotation	[α]D20 = +83° (c = 0.5, CHCl3, er = 84:16)

(3aS,7aR)-7a-methyl-3-vinyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.3 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 5.84 (ddd, J = 17.9, 10.2, 8.1 Hz, • 1H), 5.71 (ddd, J = 17.5, 10.2, 7.7 Hz, ◊ 1H), 5.03 – 4.90 (m, • 2H, ◊ 2H), 3.09 – 3.00 (m, • 1H), 2.99 – 2.90 (m, ◊ 1H), 2.52 (d, J = 10.6 Hz, • 1H), 2.43 (ddd, J = 15.3, 11.4, 6.5 Hz, ◊ 1H), 2.33 (dt, J = 15.8, 4.5 Hz, • 1H), 2.23 (dt, J = 15.3, 4.4 Hz, ◊ 1H), 2.11 – 2.02 (m, • 1H, ◊ 2H), 1.97 – 1.70 (m, • 5H, ◊ 3H), 1.68 – 1.48 (m, • 3H, ◊ 3H), 1.44 (dt, J = 13.5, 3.9 Hz, ◊ 1H), 1.09 (s, • 3H), 1.08 (s, ◊ 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ • 214.2, ◊ 213.8, ◊ 141.0, • 139.8, • 115.2, ◊ 114.3, ◊ 67.3, • 64.4, ◊ 48.2, ◊ 47.5, • 47.0, • 45.7, • 42.0, • 40.8, ◊ 40.3, ◊ 38.1, • 34.8, ◊ 34.3, ◊ 30.7, • 30.1, • 28.1, ◊ 26.7, ◊ 22.7, • 21.7
IR (neat) νmax (cm⁻¹)	2947, 2928, 1697, 1460, 1227, 910, 631, 544, 528, 521, 507, 500
HRMS (ESI)	m/z calcd. for C₁₂H₁₉O⁺ [M + H]⁺ 179.1430, found 179.1433
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.5°C/min – T = 115°C – 0 min]	For major diastereomer, er = 85:15 [t (major) = 23.6 min, t (minor) = 21.7 min]. For minor diastereomer : er = 87:13 [t (major) = 26.0 min, t (minor) = 24.6 min]

(3aS,7aR)-7a-ethyl-3-vinyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.1 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 5.83 (ddd, J = 17.0, 10.2, 8.0 Hz, • 1H), 5.69 (ddd, J = 17.1, 10.2, 7.7 Hz, ◊ 1H), 5.03 – 4.91 (m, • 2H, ◊ 2H), 3.06 – 2.98 (m, • 1H), 2.96 – 2.87 (m, ◊ 1H), 2.53 (d, J = 10.6 Hz, • 1H), 2.44 (ddd, J = 15.6, 11.0, 6.6 Hz, ◊ 1H), 2.35 – 2.28 (m, • 1H), 2.25 – 2.19 (m, ◊ 1H), 2.11 – 2.01 (m, • 1H, ◊ 2H), 1.95 – 1.46 (m, • 10H, ◊ 7H), 1.34 – 1.21 (m, ◊ 2H), 0.87 – 0.81 (m, • 3H, ◊ 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ • 214.5, ◊ 213.9, ◊ 140.7, • 139.8, • 115.3, ◊ 114.4, ◊ 66.8, • 63.9, ◊ 50.6, • 48.8, ◊ 48.3, • 46.7, • 41.8, ◊ 38.1, • 37.5, ◊ 36.8, ◊ 32.6, ◊ 31.4, ◊ 30.8, • 30.7, • 30.6, • 30.1, ◊ 22.0, • 21.0, • 9.2, ◊ 9.0
IR (neat) νmax (cm⁻¹)	2937, 2872, 1697, 1460, 1315, 1234, 999, 912, 631, 534, 509
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O⁺ [M + H]⁺ 193.1587, found 193.1579
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 0 min]	For major diastereomer, er = 85:15 [t (major) = 36.2 min, t (minor) = 34.3 min]. For minor diastereomer : er = 85:15 [t (major) = 40.7 min, t (minor) = 39.9 min]

(3aS,7aR)-7a-methyl-3-(E-4-(methylthio)but-1-en-1-yl)octahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 2.4 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 5.55 – 5.36 (m, • 2H, ◊ 2H), 3.02 (dq, J = 10.8, 7.6 Hz, • 1H), 2.97 – 2.88 (m, ◊ 1H), 2.52 (br s, • 2H, ◊ 2H), 2.48 (d, J = 10.5 Hz, • 1H), 2.41 (ddd, J = 15.2, 11.6, 6.5 Hz, ◊ 1H), 2.32 (dtt, J = 15.8, 4.2, 1.5 Hz, • 1H), 2.28 – 2.23 (m, • 2H, ◊ 2H), 2.23 – 2.09 (br s, • 3H, ◊ 3H), 2.08 – 2.00 (m, • 1H, ◊ 1H), 1.95 – 1.85 (m, • 2H, ◊ 2H), 1.83 – 1.70 (m, • 3H, ◊ 3H), 1.67 – 1.60 (m, • 1H, ◊ 1H), 1.58 – 1.47 (m, • 2H, ◊ 2H), 1.47 – 1.39 (m, ◊ 1H), 1.08 (s, • 3H), 1.07 (s, ◊ 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ • 214.4, ◊ 214.1, ◊ 134.1, • 133.0, • 129.3, ◊ 128.3, ◊ 67.7, • 64.4, ◊ 47.5, ◊ 47.3, • 46.0, • 45.6, • 42.0, ◊ 41.6, • 40.9, ◊ 40.3, • 34.8, ◊ 34.3, •◊ 34.1 (2C), •◊ 32.6 (2C), ◊ 31.2, • 30.7, • 28.1, ◊ 26.7, ◊ 22.8, • 21.7, •◊ 15.6 (2C)
IR (neat) νmax (cm⁻¹)	2972, 2359, 2339, 2255, 1693, 1377, 1086, 1045, 879, 494, 473
HRMS (ESI)	m/z calcd. for C₁₅H₂₅OS⁺ [M + H]⁺ 253.1621, found 253.1623
Chiral SFC [Column 2, isocratic 2 % MeOH / 98 % supercritical CO2 for 17 min, flow = 1.5 mL/min]	For major diastereomer, er = 95:5 [t (major) = 12.2 min, t (minor) = 11.8 min]. For minor diastereomer : er = 91:9 [t (major) = 13.0 min, t (minor) = 12.5 min]

(3aS,7aR)-3-(3-((tert-butyldiphenylsilyl)oxy)prop-1-en-2-yl)-7a-methyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.2 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.74 – 7.64 (m, • 4H, ◊ 4H), 7.45 – 7.35 (m, • 6H, ◊ 6H), 5.26 – 5.23 (m, ◊ 1H), 5.19 – 5.16 (m, • 1H), 5.01 – 4.99 (m, • 1H), 4.95 – 4.92 (m, ◊ 1H), 4.20 – 4.05 (m, • 2H, ◊ 2H), 3.09 – 3.01 (m, • 1H), 2.99 – 2.91 (m, ◊ 1H), 2.47 (d, J = 9.3 Hz, ◊ 1H), 2.40 (ddd, J = 14.9, 11.6, 6.6 Hz, • 1H), 2.31 (d, J = 10.7 Hz, • 1H), 2.23 – 2.09 (m, • 1H, ◊ 2H), 2.07 – 1.93 (m, • 1H, ◊ 1H), 1.92 – 1.76 (m, • 2H, ◊ 3H), 1.75 – 1.62 (m, • 1H, ◊ 2H), 1.64 – 1.54 (m, • 2H), 1.55 – 1.47 (m, • 1H, ◊ 1H), 1.46 – 1.38 (m, • 1H, ◊ 1H), 1.08 (s, • 3H, ◊ 3H), 1.06 (s, ◊ 9H), 1.06 (s, • 9H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ • 214.2, ◊ 213.6, ◊ 149.3, • 149.2, ◊ 135.74, ◊ 135.70, • 135.67, ◊ 134.0, ◊ 133.8, • 133.72, • 133.68, • 129.8, ◊ 129.7, • 127.8, ◊ 127.8, ◊ 127.7, • 109.01, ◊ 108.98, ◊ 67.4, • 66.1, • 65.1, ◊ 62.1, • 47.9, ◊ 46.7, • 46.0, ◊ 44.0, ◊ 41.4, • 40.1, ◊ 38.3, • 37.9, ◊ 35.5, • 34.2, • 30.5, ◊ 28.6, ◊ 27.0, • 26.9, • 26.7, ◊ 26.5, • 23.1, ◊ 21.8, ◊ 19.44, • 19.40
IR (neat) νmax (cm⁻¹)	2970, 2251, 2143, 2031, 1975, 1690, 1427, 1086, 1045, 879, 820, 741, 702, 613, 505
HRMS (ESI)	m/z calcd. for C₂₉H₃₉O₂Si⁺ [M + H]⁺ 447.2714, found 447.2718
Chiral SFC [Column 1, isocratic 1 % MeOH / 99 % supercritical CO2 for 35 min, flow = 1.5 ml/min]	For major diastereomer, er = 92:8 [t (major) = 20.7 min, t (minor) = 21.2 min]. For minor diastereomer : er = 95:5 [t (major) = 22.5 min, t (minor) = 24.1 min]

(3R,3aS,7aR)-7a-methyl-3-(prop-1-en-2-yl)octahydro-4H-inden-4-one
¹H NMR (500 MHz, CDCl₃)	δ 4.75 – 4.68 (m, 2H), 3.07 – 2.99 (m, 1H), 2.50 – 2.42 (m, 1H), 2.25 (d, J = 10.8 Hz, 1H), 2.23 – 2.17 (m, 1H), 2.07 – 1.99 (m, 1H), 1.98 – 1.91 (m, 1H), 1.90 – 1.81 (m, 1H), 1.81 – 1.73 (m, 1H), 1.72 – 1.63 (m, 5H), 1.56 – 1.53 (m, 1H), 1.45 – 1.40 (m, 1H), 1.09 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.4, 146.0, 110.9, 65.0, 51.3, 47.8, 40.4, 37.8, 34.1, 29.5, 26.5, 23.0, 19.6
IR (neat) νmax (cm⁻¹)	2972, 2264, 1975, 1375, 1088, 1045, 879, 665, 625, 517, 501, 471, 465
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O⁺ [M + H]⁺ 193.1587, found 193.1587
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.5°C/min – T = 115°C – 5 min]	For this diastereomer, er = 89:11 [t (major) = 29.8 min, t (minor) = 28.3 min]

(3aS,7aR)-3-(E-2-(furan-2-yl)vinyl)-7a-methyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.3 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.28 (dd, J = 3.7, 1.8 Hz, • 1H, ◊ 1H), 6.32 (ddd, J = 4.4, 3.3, 1.8 Hz, • 1H, ◊ 1H), 6.18 – 6.11 (m, • 2H, ◊ 3H), 6.06 (dd, J = 15.8, 7.7 Hz, • 1H), 3.20 – 3.13 (m, ◊ 1H), 3.13 – 3.06 (m, • 1H), 2.56 (dt, J = 10.2, 1.6 Hz, ◊ 1H), 2.45 (ddd, J = 15.3, 11.2, 6.5 Hz, • 1H), 2.32 (dtt, J = 15.9, 4.5, 1.5 Hz, ◊ 1H), 2.28 – 2.22 (m, • 1H), 2.15 (d, J = 9.7 Hz, • 1H), 2.14 – 1.53 (m, • 7H, ◊ 9H), 1.51 – 1.45 (m, • 1H), 1.11 (s, • 3H, ◊ 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 214.1, • 213.6, • 152.82, ◊ 152.80, ◊ 141.7, • 141.5, • 131.8, ◊ 130.5, ◊ 119.1, • 118.2, ◊ 111.3, • 111.2, ◊ 107.2, • 107.0, • 67.3, ◊ 64.8, • 47.6, • 46.9, ◊ 46.3, ◊ 45.7, ◊ 41.9, ◊ 40.8, • 40.3, • 38.2, ◊ 34.9, • 34.5, • 31.2, ◊ 30.8, ◊ 28.1, • 26.8, • 22.6, ◊ 21.8
IR (neat) νmax (cm⁻¹)	2951, 2866, 1695, 1458, 1078, 1049, 1011, 926, 725, 546
HRMS (ESI)	m/z calcd. for C₁₆H₂₁O₂⁺ [M + H]⁺ 245.1536, found 245.1543
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 17 min, flow = 1.5 mL/min]	For major diastereomer, er = 95:5 [t (major) = 5.8 min, t (minor) = 6.6 min]. For minor diastereomer : er = 96:4 [t (major) = 5.0 min, t (minor) = 5.4 min]

(3aS,7aR)-7a-methyl-3-(E-styryl)octahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.2 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.25 – 7.16 (m, • 4H, ◊ 4H), 7.13 – 7.07 (m, • 1H, ◊ 1H), 6.27 (d, J = 11.7 Hz, ◊ 1H), 6.24 (d, J = 11.6 Hz, • 1H), 6.18 (dd, J = 15.8, 8.0 Hz, ◊ 1H), 6.03 (dd, J = 15.8, 7.8 Hz, • 1H), 3.18 – 3.10 (m, ◊ 1H), 3.10 – 3.03 (m, • 1H), 2.50 (d, J = 10.2 Hz, ◊ 1H), 2.40 (ddd, J = 15.2, 11.2, 6.5 Hz, • 1H), 2.27 – 2.13 (m, • 1H, ◊ 1H), 2.12 – 2.03 (m, • 2H), 2.01 – 1.90 (m, ◊ 2H), 1.89 – 1.66 (m, • 3H, ◊ 5H), 1.64 – 1.46 (m, • 3H, ◊ 2H), 1.40 (dt, J = 13.6, 3.9 Hz, • 1H), 1.05 (s, ◊ 3H), 1.04 (s, • 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 214.1, • 213.6, ◊ 137.4, • 137.3, • 132.8, ◊ 131.6, ◊ 130.3, • 129.6, ◊ 128.6, • 128.5, ◊ 127.3, • 127.2, • 126.3, ◊ 126.2, • 67.4, ◊ 64.7, • 47.6, • 47.3, ◊ 46.2, ◊ 45.8, ◊ 41.9, ◊ 40.6, • 40.3, • 38.2, ◊ 35.0, • 34.4, • 31.2, ◊ 30.5, ◊ 28.2, • 26.8, • 22.7, ◊ 21.8
IR (neat) νmax (cm⁻¹)	2974, 1705, 1688, 1452, 1375, 1088, 1047, 881, 631, 538, 521, 501
HRMS (ESI)	m/z calcd. for C₁₈H₂₂ONa⁺ [M + Na]⁺ 277.1563, found 277.1568
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 85:15 [t (major) = 9.7 min, t (minor) = 10.3 min]. For minor diastereomer : er = 85:15 [t (major) = 8.8 min, t (minor) = 9.2 min]

(3aS,7aR)-3-(E-4-methoxystyryl)-7a-methyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.6 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.27 – 7.22 (m, • 2H, ◊ 2H), 6.85 – 6.79 (m, • 2H, ◊ 2H), 6.29 (d, J = 10.8 Hz, ◊ 1H), 6.25 (d, J = 10.8 Hz, • 1H), 6.10 (dd, J = 15.8, 8.3 Hz, ◊ 1H), 5.96 (dd, J = 15.8, 7.8 Hz, • 1H), 3.79 (s, ◊ 3H), 3.79 (s, • 3H), 3.24 – 3.17 (m, ◊ 1H), 3.16 – 3.08 (m, • 1H), 2.56 (d, J = 10.2 Hz, ◊ 1H), 2.48 (ddd, J = 15.2, 11.3, 6.5 Hz, • 1H), 2.34 – 1.74 (m, • 6H, ◊ 8H), 1.72 – 1.53 (m, • 3H, ◊ 2H), 1.50 – 1.44 (m, • 1H), 1.12 (s, ◊ 3H), 1.11 (s, • 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 214.3, • 213.8, ◊ 159.1, • 159.0, • 130.7, ◊ 130.3, • 130.2, ◊ 129.8, ◊ 129.5, • 129.0, • 127.44, ◊ 127.38, ◊ 114.1, • 114.0, • 67.6, ◊ 64.8, ◊ 55.43, • 55.42, • 47.6, • 47.4, ◊ 46.3, ◊ 45.8, ◊ 41.9, ◊ 40.8, • 40.3, • 38.2, ◊ 35.0, • 34.5, • 31.3, ◊ 30.7, ◊ 28.2, • 26.8, • 22.8, ◊ 21.8
IR (neat) νmax (cm⁻¹)	2361, 2341, 2257, 1510, 1248, 1086, 1045, 878, 554, 517, 461
HRMS (ESI)	m/z calcd. for C₁₉H₂₅O₂⁺ [M + H]⁺ 285.1849, found 285.1849
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 92:8 [t (major) = 12.3 min, t (minor) = 14.8 min]. For minor diastereomer : er = 86:14 [t (major) = 10.8 min, t (minor) = 11.4 min]

(3aS,7aR)-3-(E-4-fluorostyryl)-7a-methyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.1 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.29 – 7.24 (m, • 2H, ◊ 2H), 6.99 – 6.92 (m, • 2H, ◊ 2H), 6.30 (d, J = 10.7 Hz, ◊ 1H), 6.27 (d, J = 10.6 Hz, • 1H), 6.18 (dd, J = 15.8, 8.2 Hz, ◊ 1H), 6.01 (dd, J = 15.8, 7.8 Hz, • 1H), 3.24 – 3.16 (m, ◊ 1H), 3.16 – 3.09 (m, • 1H), 2.57 (d, J = 10.1 Hz, ◊ 1H), 2.47 (ddd, J = 15.3, 11.2, 6.5 Hz, • 1H), 2.32 (dtt, J = 15.5, 4.8, 1.3 Hz, ◊ 1H), 2.28 – 2.23 (m, • 1H), 2.18 – 2.10 (m, • 2H), 2.07 – 1.74 (m, • 3H, ◊ 7H), 1.73 – 1.64 (m, • 2H, ◊ 1H), 1.62 – 1.54 (m, • 1H, ◊ 1H), 1.51 – 1.45 (m, • 1H), 1.13 (s, ◊ 3H), 1.12 (s, • 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 214.1, • 213.7, ◊ 162.21 (d, J = 246.1 Hz), • 162.16 (d, J = 246.0 Hz), ◊ 133.6 (d, J = 3.3 Hz), • 133.5 (d, J = 3.3 Hz), • 132.6 (d, J = 2.2 Hz), ◊ 131.5 (d, J = 2.1 Hz), ◊ 129.2, • 128.4, • 127.8 (d, J = 8.0 Hz), ◊ 127.7 (d, J = 8.0 Hz), ◊ 115.5 (d, J = 21.6 Hz), • 115.4 (d, J = 21.5 Hz), • 67.4, ◊ 64.7, • 47.6, • 47.3, ◊ 46.1, ◊ 45.9, ◊ 41.9, ◊ 40.4, • 40.3, • 38.2, ◊ 35.1, • 34.5, • 31.2, ◊ 30.6, ◊ 28.3, • 26.8, • 22.7, ◊ 21.9
¹⁹F NMR {¹H} (471 MHz, CDCl₃)	◊ -115.2, • -115.4
IR (neat) νmax (cm⁻¹)	2974, 1688, 1508, 1227, 1086, 1047, 879, 527, 467
HRMS (ESI)	m/z calcd. for C₁₈H₂₂FO⁺ [M + H]⁺ 273.1649, found 273.1652
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 91:9 [t (major) = 5.7 min, t (minor) = 6.5 min]. For minor diastereomer : er = 86:14 [t (major) = 5.2 min, t (minor) = 5.4 min]

(3aS,7aR)-3-(E-4-chlorostyryl)-7a-methyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.3 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.24 – 7.20 (m, • 4H, ◊ 4H), 6.31 – 6.23 (m, • 1H, ◊ 2H), 6.08 (dd, J = 15.8, 7.8 Hz, • 1H), 3.24 – 3.16 (m, ◊ 1H), 3.16 – 3.09 (m, • 1H), 2.57 (d, J = 10.0 Hz, ◊ 1H), 2.46 (ddd, J = 15.4, 11.2, 6.5 Hz, • 1H), 2.32 (dtt, J = 15.6, 5.0, 1.4 Hz, ◊ 1H), 2.28 – 2.22 (m, • 1H), 2.17 – 2.10 (m, • 2H), 2.06 – 1.73 (m, • 3H, ◊ 7H), 1.72 – 1.64 (m, • 2H, ◊ 1H), 1.62 – 1.55 (m, • 1H, ◊ 1H), 1.51 – 1.45 (m, • 1H), 1.13 (s, ◊ 3H), 1.12 (s, • 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 213.9, • 213.6, ◊ 135.95, • 135.86, • 133.6, ◊ 132.8, • 132.7, ◊ 132.5, ◊ 129.1, ◊ 128.7, • 128.6, • 128.4, • 127.5, ◊ 127.4, • 67.3, ◊ 64.6, • 47.5, • 47.2, ◊ 46.04, ◊ 45.96, ◊ 41.9, • 40.28, ◊ 40.28, • 38.2, ◊ 35.1, • 34.4, • 31.1, ◊ 30.4, ◊ 28.4, • 26.8, • 22.6, ◊ 21.9
IR (neat) νmax (cm⁻¹)	2968, 2361, 2341, 2251, 1693, 1491, 1088, 1047, 879, 806, 623, 538, 527, 467
HRMS (ESI)	m/z calcd. for C₁₈H₂₂ClO⁺ [M + H]⁺ 289.1354, found 289.1355
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 93:7 [t (major) = 9.2 min, t (minor) = 10.7 min]. For minor diastereomer : er = 87:13 [t (major) = 8.2 min, t (minor) = 8.7 min]

(3aS,7aR)-3-(E-3-chlorostyryl)-7a-methyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.1 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.33 – 7.27 (m, • 1H, ◊ 1H), 7.23 – 7.10 (m, • 3H, ◊ 3H), 6.34 – 6.23 (m, • 1H, ◊ 2H), 6.12 (dd, J = 15.8, 7.7 Hz, • 1H), 3.23 – 3.16 (m, ◊ 1H), 3.16 – 3.09 (m, • 1H), 2.57 (d, J = 10.0 Hz, ◊ 1H), 2.46 (ddd, J = 15.4, 11.2, 6.5 Hz, • 1H), 2.32 (dtt, J = 15.6, 5.1, 1.5 Hz, ◊ 1H), 2.28 – 2.22 (m, • 1H), 2.18 – 2.10 (m, • 2H), 2.06 – 1.73 (m, • 3H, ◊ 7H), 1.72 – 1.64 (m, • 2H, ◊ 1H), 1.62 – 1.54 (m, • 1H, ◊ 1H), 1.51 – 1.45 (m, • 1H), 1.13 (s, ◊ 3H), 1.12 (s, • 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 213.9, • 213.5, ◊ 139.3, • 139.2, • 134.55, • 134.49, ◊ 134.46, ◊ 133.4, ◊ 129.8, • 129.7, ◊ 129.1, • 128.3, ◊ 127.2, • 127.1, ◊ 126.2, • 126.0, ◊ 124.57, • 124.55, ◊ 67.3, • 64.6, • 47.5, • 47.1, ◊ 46.0, ◊ 41.9, • 40.3, ◊ 40.2, • 38.2, ◊ 35.1, • 34.4, ◊ 31.1, • 30.4, ◊ 28.4, • 26.8, • 22.6, ◊ 21.9
IR (neat) νmax (cm⁻¹)	2972, 1693, 1088, 1047, 879, 627, 521, 468
HRMS (ESI)	m/z calcd. for C₁₈H₂₂ClO⁺ [M + H]⁺ 289.1354, found 289.1356
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 93:7 [t (major) = 9.8 min, t (minor) = 10.8 min]. For minor diastereomer : er = 93:7 [t (major) = 8.3 min, t (minor) = 8.7 min]

(3aS,7aR)-3-(E-2-chlorostyryl)-7a-methyloctahydro-4H-inden-4-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.2 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 7.49 (dd, J = 7.7, 1.6 Hz, • 1H), 7.45 (dd, J = 7.7, 1.6 Hz, ◊ 1H), 7.32 – 7.28 (m, • 1H, ◊ 1H), 7.20 – 7.15 (m, • 1H, ◊ 1H), 7.15 – 7.09 (m, • 1H, ◊ 1H), 6.75 – 6.67 (m, • 1H, ◊ 1H), 6.32 (dd, J = 15.8, 8.0 Hz, ◊ 1H), 6.09 (dd, J = 15.7, 7.9 Hz, • 1H), 3.30 – 3.14 (m, • 1H, ◊ 1H), 2.60 (d, J = 9.9 Hz, ◊ 1H), 2.48 (ddd, J = 15.3, 11.1, 6.5 Hz, • 1H), 2.34 (dtt, J = 15.5, 5.2, 1.4 Hz, ◊ 1H), 2.30 – 2.23 (m, • 1H), 2.21 – 2.13 (m, • 2H), 2.10 – 1.75 (m, • 3H, ◊ 7H), 1.74 – 1.65 (m, • 2H, ◊ 1H), 1.64 – 1.54 (m, • 1H, ◊ 1H), 1.51 – 1.46 (m, • 1H), 1.15 (s, ◊ 3H), 1.12 (s, • 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 213.9, • 213.5, ◊ 135.65, • 135.63, • 135.4, ◊ 134.8, ◊ 132.9, • 132.8, ◊ 129.7, • 129.6, ◊ 128.26, • 128.25, • 127.0, ◊ 126.92, • 126.90, • 126.8, ◊ 126.4, ◊ 125.8, • 67.5, ◊ 64.6, • 47.52, • 47.49, ◊ 46.2, ◊ 46.0, ◊ 42.0, • 40.3, ◊ 40.0, • 38.2, ◊ 35.1, ◊ 34.5, • 31.1, • 30.2, ◊ 28.6, • 26.8, • 22.7, ◊ 21.9
IR (neat) νmax (cm⁻¹)	2968, 1697, 1379, 1088, 1047, 879, 754, 623, 555, 546, 528, 467
HRMS (ESI)	m/z calcd. for C₁₈H₂₂ClO⁺ [M + H]⁺ 289.1354, found 289.1355
Chiral SFC [Column 4, isocratic 2 % MeOH / 98 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 93:7 [t (major) = 18.2 min, t (minor) = 17.4 min]. For minor diastereomer : er = 92:8 [t (major) = 15.9 min, t (minor) = 16.2 min]

(4aS,8R,8aS)-4a-methyl-8-vinyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 6.17 (ddd, J = 17.4, 10.2, 7.3 Hz, 1H), 5.01 – 4.81 (m, 2H), 2.44 – 2.34 (m, 2H), 2.32 – 2.19 (m, 2H), 1.90 – 1.79 (m, 3H), 1.75 – 1.68 (m, 1H), 1.64 – 1.39 (m, 5H), 1.18 (s, 3H), 1.05 (d, J = 13.2 Hz, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.2, 144.0, 112.9, 60.3, 43.4, 40.9, 40.6, 39.0, 31.9, 27.2, 26.7, 22.8, 21.5
IR (neat) νmax (cm⁻¹)	2928, 1707, 1088, 1047, 879, 631, 534, 521, 507, 492
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O⁺ [M + H]⁺ 193.1587, found 193.1588
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 0 min]	For major diastereomer, er = 86:14 [t (major) = 33.7 min, t (minor) = 33.1 min]

(4aS,8S,8aS)-4a-methyl-8-vinyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 5.52 (ddd, J = 17.1, 10.2, 8.5 Hz, 1H), 4.99 – 4.85 (m, 2H), 2.46 (tdd, J = 12.0, 8.6, 3.7 Hz, 1H), 2.34 (td, J = 13.8, 7.3 Hz, 1H), 2.26 – 2.11 (m, 2H), 1.99 – 1.92 (m, 1H), 1.91 – 1.82 (m, 1H), 1.80 (d, 1H), 1.78 – 1.73 (m, 1H), 1.72 – 1.51 (m, 3H), 1.22 – 1.06 (m, 3H), 0.90 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.6, 141.0, 114.3, 64.9, 42.5, 39.3, 37.9, 37.6, 32.6, 29.5, 28.1, 22.5, 21.1
IR (neat) νmax (cm⁻¹)	2928, 2870, 1705, 1448, 1311, 1232, 912, 644, 505, 469
HRMS (ESI)	m/z calcd. for C₁₃H₂₁O⁺ [M + H]⁺ 193.1587, found 193.1590
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 5 min]	For minor diastereomer, er = 86:14 [t (major) = 48.0 min, t (minor) = 42.3 min]

(4aS,8R,8aS)-4a-ethyl-8-vinyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 6.18 (ddd, J = 17.5, 10.2, 7.5 Hz, 1H), 4.97 – 4.84 (m, 2H), 2.41 (d, J = 2.7 Hz, 1H), 2.34 – 2.19 (m, 3H), 1.92 – 1.81 (m, 3H), 1.77 – 1.63 (m, 2H), 1.61 – 1.35 (m, 6H), 1.16 – 1.10 (m, 1H), 0.89 (t, J = 7.5 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.8, 144.1, 112.9, 57.9, 43.3, 43.1, 38.5, 35.4, 29.9, 29.8, 26.4, 22.6, 20.9, 7.6
IR (neat) νmax (cm⁻¹)	2930, 2866, 1709, 1452, 1092, 1047, 906, 879, 615, 569
HRMS (ESI)	m/z calcd. for C₁₄H₂₃O⁺ [M + H]⁺ 207.1743, found 207.1739
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 5 min]	For major diastereomer, er = 81:19 [t (major) = 48.7 min, t (minor) = 48.2 min]

(4aS,8S,8aS)-4a-ethyl-8-vinyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 5.52 (ddd, J = 17.1, 10.2, 8.6 Hz, 1H), 4.98 – 4.85 (m, 2H), 2.49 (tdd, J = 12.0, 8.6, 3.7 Hz, 1H), 2.33 (td, J = 13.9, 7.4 Hz, 1H), 2.19 – 2.13 (m, 1H), 2.08 (td, J = 14.0, 4.7 Hz, 1H), 1.94 – 1.89 (m, 1H), 1.81 (d, J = 11.5 Hz, 1H), 1.79 – 1.72 (m, 3H), 1.66 – 1.60 (m, 3H), 1.44 – 1.34 (m, 1H), 1.33 – 1.20 (m, 1H), 1.16 – 1.04 (m, 2H), 0.78 (t, J = 7.5 Hz, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.6, 141.1, 114.3, 64.4, 42.5, 39.7, 38.0, 34.7, 32.8, 32.1, 25.6, 21.9, 20.8, 7.0
IR (neat) νmax (cm⁻¹)	2930, 1709, 1468, 916, 617, 546, 509, 457
HRMS (ESI)	m/z calcd. for C₁₄H₂₃O⁺ [M + H]⁺ 207.1743, found 207.1733
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.2°C/min – T = 110°C – 10 min]	For minor diastereomer, er = 81:19 [t (major) = 66.5 min, t (minor) = 66.3 min]

(4aS,8R,8aS)-4a-methyl-8-(E-4-(methylthio)but-1-en-1-yl)octahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 5.89 (ddt, J = 15.4, 8.1, 1.5 Hz, 1H), 5.38 (dtd, J = 15.4, 6.7, 1.0 Hz, 1H), 2.50 (br s, 2H), 2.36 (ddt, J = 12.1, 8.0, 4.0 Hz, 1H), 2.32 – 2.30 (m, 1H), 2.30 – 2.19 (m, 4H), 2.10 (br s, 3H), 1.90 – 1.78 (m, 3H), 1.74 – 1.67 (m, 1H), 1.63 – 1.50 (m, 3H), 1.46 – 1.38 (m, 2H), 1.16 (s, 3H), 1.06 – 0.99 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.4, 136.9, 127.1, 60.5, 43.5, 40.9, 40.6, 38.2, 34.4, 32.4, 31.9, 27.22, 27.20, 22.8, 21.5, 15.5
IR (neat) νmax (cm⁻¹)	2943, 2359, 2339, 2262, 2251, 1709, 1643, 542, 505, 488, 476, 457
HRMS (ESI)	m/z calcd. for C₁₆H₂₇OS⁺ [M + H]⁺ 267.1777, found 267.1780
Chiral SFC [Column 2, isocratic 2 % MeOH / 98 % supercritical CO2 for 17 min, flow = 1.5 mL/min]	For major diastereomer, er = 94:6 [t (major) = 9.7 min, t (minor) = 11.5 min]

(4aS,8S,8aS)-4a-methyl-8-(E-4-(methylthio)but-1-en-1-yl)octahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 5.40 (dt, J = 15.4, 6.7 Hz, 1H), 5.19 (ddt, J = 15.3, 8.6, 1.4 Hz, 1H), 2.49 – 2.38 (m, 3H), 2.33 (td, J = 13.8, 7.3 Hz, 1H), 2.24 – 2.16 (m, 3H), 2.15 – 2.09 (m, 1H), 2.07 (s, 3H), 1.99 – 1.91 (m, 1H), 1.90 – 1.79 (m, 1H), 1.78 – 1.71 (m, 2H), 1.68 – 1.56 (m, 2H), 1.55 – 1.49 (m, 1H), 1.16 (td, J = 13.5, 4.7 Hz, 1H), 1.11 – 1.02 (m, 2H), 0.89 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.6, 134.1, 128.2, 65.1, 41.2, 39.3, 37.9, 37.6, 34.3, 33.0, 32.2, 29.5, 28.0, 22.6, 21.1, 15.6
IR (neat) νmax (cm⁻¹)	2926, 1697, 1433, 1379, 1310, 1232, 1086, 1047, 966, 879, 725, 561, 527, 459
HRMS (ESI)	m/z calcd. for C₁₆H₂₇OS⁺ [M + H]⁺ 267.1777, found 267.1782
Chiral SFC [Column 2, isocratic 2 % MeOH / 98 % supercritical CO2 for 27 min, flow = 1.5 mL/min]	For major diastereomer, er = 91:9 [t (major) = 17.3 min, t (minor) = 16.3 min]

(4aS,8R,8aR)-4a,8-dimethyl-8-vinyloctahydronaphthalen-1(2H)-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 4 : 1) of which only the signals of the major diastereomer are reported
¹H NMR (500 MHz, CDCl₃)	δ 6.31 (dd, J = 17.5, 11.0 Hz, 1H), 5.05 (dd, J = 11.0, 1.2 Hz, 1H), 4.96 (dd, J = 17.5, 1.3 Hz, 1H), 2.53 (ddd, J = 15.9, 12.6, 8.6 Hz, 1H), 2.41 – 2.08 (m, 4H), 1.96 (s, 1H), 1.92 – 1.75 (m, 3H), 1.71 – 1.60 (m, 1H), 1.51 – 1.43 (m, 1H), 1.24 (tt, J = 13.7, 3.5 Hz, 1H), 1.14 – 1.05 (m, 1H), 1.06 (s, 3H), 0.88 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.2, 144.7, 113.3, 68.4, 40.7, 40.1, 39.6, 39.0, 36.6, 31.0, 30.5, 28.9, 21.2, 18.0
IR (neat) νmax (cm⁻¹)	2972, 1375, 1088, 1047, 879, 631, 567, 525, 503
HRMS (ESI)	m/z calcd. for C₁₄H₂₃O⁺ [M + H]⁺ 207.1743, found 207.1742
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 5 min]	For major diastereomer, er = 89:11 [t (major) = 51.7 min, t (minor) = 50.2 min]. For minor diastereomer : er = 95:5 [t (major) = 55.8 min, t (minor) = 54.8 min]

(4aS,8aS)-4a-methyl-8-(prop-1-en-2-yl)octahydronaphthalen-1(2H)-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 3.2 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 4.73 – 4.68 (m, ◊ 2H), 4.68 – 4.62 (m, • 2H), 3.08 – 2.98 (m, ◊ 1H), 2.58 (td, J = 12.0, 3.2 Hz, • 1H), 2.48 – 2.38 (m, • 1H, ◊ 1H), 2.28 – 2.18 (m, • 1H, ◊ 2H), 2.12 – 2.06 (m, • 1H), 2.06 – 2.00 (m, • 1H, ◊ 1H), 1.98 – 1.91 (m, • 1H, ◊ 1H), 1.89 – 1.76 (m, • 1H, ◊ 2H), 1.71 – 1.60 (m, • 6H, ◊ 6H), 1.58 – 1.51 (m, • 1H), 1.45 – 1.40 (m, ◊ 1H), 1.34 – 1.15 (m, • 2H, ◊ 2H), 1.11 – 1.05 (m, • 1H, ◊ 3H), 0.91 (s, • 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ • 214.6, ◊ 214.4, • 147.1, ◊ 146.0, • 111.7, ◊ 110.9, ◊ 65.0, • 62.5, ◊ 51.3, • 46.4, ◊ 40.5, ◊ 40.4, • 39.5, ◊ 37.83, • 37.75, • 37.3, ◊ 34.1, • 31.5, ◊ 29.47, • 29.45, • 28.2, ◊ 26.5, ◊ 23.0, • 22.6, •◊ 21.5, ◊ 19.6, • 17.7
IR (neat) νmax (cm⁻¹)	2918, 2866, 1707, 1448, 891, 644, 631, 544, 532, 527, 500, 494
HRMS (ESI)	m/z calcd. for C₁₄H₂₃O⁺ [M + H]⁺ 207.1743, found 207.1740
Chiral GC [Agilent CP Chirasil-Dex-CB, T = 100°C – 1 min – 0.3°C/min – T = 115°C – 5 min]	For major diastereomer, er = 88:12 [t (major) = 58.2 min, t (minor) = 51.2 min]. For minor diastereomer : er = 85:15 [t (major) = 15.5 min, t (minor) = 2.6 min]

(4aS,8R,8aS)-8-(E-2-(furan-2-yl)vinyl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.28 (d, J = 1.8 Hz, 1H), 6.54 (dd, J = 16.0, 8.1 Hz, 1H), 6.31 (dd, J = 3.3, 1.8 Hz, 1H), 6.15 (dd, J = 16.1, 1.1 Hz, 1H), 6.12 (d, J = 3.2 Hz, 1H), 2.51 (ddtd, J = 12.1, 8.0, 4.0, 1.2 Hz, 1H), 2.40 (d, J = 2.9 Hz, 1H), 2.32 – 2.21 (m, 2H), 1.99 – 1.90 (m, 1H), 1.89 – 1.83 (m, 2H), 1.77 – 1.70 (m, 1H), 1.68 – 1.43 (m, 5H), 1.20 (s, 3H), 1.07 (dtt, J = 13.1, 3.2, 1.4 Hz, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.0, 153.6, 141.3, 134.9, 117.5, 111.1, 106.1, 60.4, 43.4, 40.9, 40.6, 38.5, 31.8, 27.2, 26.9, 22.8, 21.5
IR (neat) νmax (cm⁻¹)	2974, 2895, 1379, 1088, 1045, 879, 579
HRMS (ESI)	m/z calcd. for C₁₇H₂₃O₂⁺ [M + H]⁺ 259.1693, found 259.1695
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 17 min, flow = 1.5 mL/min]	For major diastereomer, er = 92:8 [t (major) = 6.6 min, t (minor) = 7.8 min]

(4aS,8S,8aS)-8-(E-2-(furan-2-yl)vinyl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.27 – 7.27 (m, 1H), 6.30 (dd, J = 3.2, 1.8 Hz, 1H), 6.16 – 6.11 (m, 2H), 5.87 (dd, J = 15.9, 8.6 Hz, 1H), 2.59 (tdd, J = 12.0, 8.6, 3.8 Hz, 1H), 2.37 (dt, J = 13.7, 6.9 Hz, 1H), 2.29 – 2.08 (m, 3H), 2.02 – 1.93 (m, 1H), 1.93 – 1.78 (m, 2H), 1.73 – 1.61 (m, 2H), 1.59 – 1.53 (m, 1H), 1.34 – 1.08 (m, 3H), 0.92 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.2, 152.7, 141.6, 131.3, 118.2, 111.2, 107.0, 64.9, 41.3, 39.3, 37.9, 37.7, 33.0, 29.6, 28.0, 22.6, 21.1
IR (neat) νmax (cm⁻¹)	2972, 2887, 1379, 1088, 1045, 879, 663, 617, 467
HRMS (ESI)	m/z calcd. for C₁₇H₂₃O₂⁺ [M + H]⁺ 259.1693, found 259.1695
Chiral SFC [Column 1, isocratic 2.5 % MeOH / 97.5 % supercritical CO2 for 15 min, flow = 1.5 mL/min]	For minor diastereomer, er = 93:7 [t (major) = 8.4 min, t (minor) = 9.4 min]

(4aS,8R,8aS)-4a-methyl-8-(E-styryl)octahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.36 – 7.32 (m, 2H), 7.29 – 7.23 (m, 2H), 7.18 – 7.14 (m, 1H), 6.67 (dd, J = 15.9, 8.3 Hz, 1H), 6.31 (d, J = 15.8 Hz, 1H), 2.61 – 2.53 (m, 1H), 2.41 (d, J = 2.9 Hz, 1H), 2.32 – 2.21 (m, 2H), 2.01 – 1.84 (m, 3H), 1.78 – 1.70 (m, 1H), 1.67 – 1.45 (m, 5H), 1.22 (s, 3H), 1.10 – 1.05 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.2, 138.1, 135.9, 128.8, 128.5, 126.9, 126.2, 60.7, 43.4, 41.0, 40.6, 38.9, 31.8, 27.2, 27.1, 22.8, 21.5
IR (neat) νmax (cm⁻¹)	2966, 1703, 1447, 1379, 1088, 1047, 968, 879, 748, 694, 615, 542, 461
HRMS (ESI)	m/z calcd. for C₁₉H₂₅O⁺ [M + H]⁺ 269.1900, found 269.1903
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 90:10 [t (major) = 7.6 min, t (minor) = 8.5 min]

(4aS,8S,8aS)-4a-methyl-8-(E-styryl)octahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.30 – 7.23 (m, 4H), 7.19 – 7.15 (m, 1H), 6.32 (d, J = 15.8 Hz, 1H), 5.92 (dd, J = 15.8, 8.7 Hz, 1H), 2.64 (tdd, J = 11.9, 8.5, 3.7 Hz, 1H), 2.43 – 2.35 (m, 1H), 2.29 – 2.21 (m, 1H), 2.19 – 2.12 (m, 1H), 2.01 – 1.95 (m, 1H), 1.94 – 1.80 (m, 3H), 1.77 – 1.58 (m, 3H), 1.25 – 1.09 (m, 3H), 0.93 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.3, 137.3, 132.6, 129.6, 128.5, 127.3, 126.4, 65.0, 41.6, 39.3, 37.9, 33.1, 29.9, 29.6, 28.0, 22.6, 21.2
IR (neat) νmax (cm⁻¹)	2974, 1452, 1375, 1086, 1045, 879, 692, 627, 540, 521, 461
HRMS (ESI)	m/z calcd. for C₁₉H₂₅O⁺ [M + H]⁺ 269.1900, found 269.1906
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 89:11 [t (major) = 12.7 min, t (minor) = 15.2 min]

(4aS,8R,8aS)-8-(E-4-fluorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.32 – 7.27 (m, 2H), 6.98 – 6.91 (m, 2H), 6.58 (dd, J = 15.9, 8.3 Hz, 1H), 6.27 (d, J = 15.9 Hz, 1H), 2.54 (ddt, J = 11.8, 8.0, 3.7 Hz, 1H), 2.40 (d, J = 2.9 Hz, 1H), 2.33 – 2.21 (m, 2H), 1.99 – 1.85 (m, 3H), 1.78 – 1.70 (m, 1H), 1.68 – 1.44 (m, 5H), 1.22 (s, 3H), 1.10 – 1.05 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.3, 162.0 (d, J = 245.3 Hz), 135.7 (d, J = 2.2 Hz), 134.2 (d, J = 3.1 Hz), 127.6 (d, J = 6.6 Hz), 127.6, 115.3 (d, J = 21.4 Hz), 60.7, 43.4, 41.0, 40.6, 38.8, 31.8, 27.2, 27.1, 22.8, 21.5
¹⁹F NMR {¹H} (471 MHz, CDCl₃)	-116.0
IR (neat) νmax (cm⁻¹)	2920, 1707, 1508, 1229, 1049, 633, 546, 534, 527, 492
HRMS (ESI)	m/z calcd. for C₁₉H₂₄FO⁺ [M + H]⁺ 287.1806, found 287.1809
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 92:8 [t (major) = 6.1 min, t (minor) = 6.5 min]

(4aS,8S,8aS)-8-(E-4-fluorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.25 – 7.21 (m, 2H), 6.97 – 6.91 (m, 2H), 6.28 (d, J = 15.8 Hz, 1H), 5.83 (dd, J = 15.8, 8.6 Hz, 1H), 2.62 (tdd, J = 11.8, 8.7, 3.5 Hz, 1H), 2.38 (td, J = 13.8, 7.3 Hz, 1H), 2.28 – 2.13 (m, 2H), 2.01 – 1.95 (m, 1H), 1.92 – 1.80 (m, 3H), 1.74 – 1.51 (m, 3H), 1.24 – 1.10 (m, 3H), 0.93 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.3, 162.2 (d, J = 246.1 Hz), 133.5 (d, J = 3.1 Hz), 132.4 (d, J = 2.2 Hz), 128.4, 127.8 (d, J = 8.0 Hz), 115.4 (d, J = 21.5 Hz), 65.0, 41.6, 39.3, 37.9, 37.7, 33.1, 29.5, 28.0, 22.5, 21.1
¹⁹F NMR {¹H} (471 MHz, CDCl₃)	-115.3
IR (neat) νmax (cm⁻¹)	2924, 1703, 1508, 1450, 1225, 1157, 962, 837, 810, 644, 625, 527, 507
HRMS (ESI)	m/z calcd. for C₁₉H₂₄FO⁺ [M + H]⁺ 287.1806, found 287.1808
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For minor diastereomer, er = 92:8 [t (major) = 9.5 min, t (minor) = 10.1 min]

(4aS,8R,8aS)-8-(E-4-chlorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.27 – 7.20 (m, 4H), 6.64 (dd, J = 15.9, 8.3 Hz, 1H), 6.26 (d, J = 15.9 Hz, 1H), 2.59 – 2.52 (m, 1H), 2.40 (d, J = 3.0 Hz, 1H), 2.32 – 2.21 (m, 2H), 1.99 – 1.83 (m, 3H), 1.79 – 1.70 (m, 1H), 1.68 – 1.44 (m, 5H), 1.22 (s, 3H), 1.11 – 1.05 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.2, 136.7, 136.6, 132.4, 128.6, 127.6, 127.4, 60.6, 43.4, 41.0, 40.6, 38.8, 31.8, 27.2, 27.0, 22.7, 21.5
IR (neat) νmax (cm⁻¹)	2972, 2368, 2264, 1375, 1088, 1047, 879, 631, 550, 534, 521, 503, 492, 455
HRMS (ESI)	m/z calcd. for C₁₉H₂₃ClONa⁺ [M + Na]⁺ 325.1330, found 325.1335
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 91:9 [t (major) = 9.5 min, t (minor) = 9.9 min]

(4aS,8S,8aS)-8-(E-4-chlorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.24 – 7.18 (m, 4H), 6.27 (d, J = 15.8 Hz, 1H), 5.89 (dd, J = 15.8, 8.6 Hz, 1H), 2.63 (tdd, J = 11.8, 8.7, 3.5 Hz, 1H), 2.37 (td, J = 13.8, 7.3 Hz, 1H), 2.24 (td, J = 13.7, 4.9 Hz, 1H), 2.19 – 2.13 (m, 1H), 2.01 – 1.94 (m, 1H), 1.93 – 1.79 (m, 3H), 1.76 – 1.55 (m, 3H), 1.25 – 1.10 (m, 3H), 0.93 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.2, 135.8, 133.4, 132.9, 128.7, 128.4, 127.6, 64.9, 41.5, 39.3, 37.9, 37.6, 33.0, 29.5, 28.0, 22.5, 21.1
IR (neat) νmax (cm⁻¹)	2922, 2363, 2160, 1690, 1456, 1092, 1049, 883, 631, 550, 534, 527, 501, 492
HRMS (ESI)	m/z calcd. for C₁₉H₂₃ClONa⁺ [M + Na]⁺ 325.1330, found 325.1332
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For minor diastereomer, er = 92:8 [t (major) = 15.0 min, t (minor) = 15.9 min]

(4aS,8R,8aS)-8-(E-3-chlorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.33 – 7.31 (m, 1H), 7.21 – 7.16 (m, 2H), 7.12 (dt, J = 6.8, 2.1 Hz, 1H), 6.67 (dd, J = 15.9, 8.2 Hz, 1H), 6.25 (d, J = 15.9 Hz, 1H), 2.58 – 2.53 (m, 1H), 2.40 (d, J = 2.9 Hz, 1H), 2.32 – 2.22 (m, 2H), 1.98 – 1.84 (m, 3H), 1.78 – 1.71 (m, 1H), 1.68 – 1.45 (m, 5H), 1.22 (s, 3H), 1.10 – 1.06 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.1, 140.0, 137.6, 134.5, 129.7, 127.5, 126.8, 126.1, 124.4, 60.6, 43.4, 41.0, 40.6, 38.7, 31.8, 27.2, 26.9, 22.7, 21.5
IR (neat) νmax (cm⁻¹)	2974, 2164, 1975, 1375, 1088, 1045, 879, 800, 662, 627, 536, 519, 500, 494, 471, 463
HRMS (ESI)	m/z calcd. for C₁₉H₂₃ClONa⁺ [M + Na]⁺ 325.1330, found 325.1336
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 93:7 [t (major) = 9.2 min, t (minor) = 10.0 min]

(4aS,8S,8aS)-8-(E-3-chlorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.27 – 7.26 (m, 1H), 7.19 – 7.13 (m, 3H), 6.25 (d, J = 15.8 Hz, 1H), 5.93 (dd, J = 15.8, 8.7 Hz, 1H), 2.63 (tdd, J = 11.8, 8.7, 3.4 Hz, 1H), 2.37 (td, J = 13.8, 7.3 Hz, 1H), 2.23 (td, J = 13.8, 4.9 Hz, 1H), 2.18 – 2.14 (m, 1H), 2.00 – 1.95 (m, 1H), 1.92 – 1.80 (m, 3H), 1.76 – 1.55 (m, 3H), 1.26 – 1.10 (m, 3H), 0.93 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.2, 139.2, 134.5, 134.3, 129.7, 128.3, 127.2, 126.3, 124.6, 64.8, 41.5, 39.2, 37.9, 37.6, 32.9, 29.5, 28.0, 22.5, 21.1
IR (neat) νmax (cm⁻¹)	2966, 2035, 1975, 1454, 1377, 1088, 1045, 879, 662, 617, 527, 519, 507, 467, 457
HRMS (ESI)	m/z calcd. for C₁₉H₂₃ClONa⁺ [M + Na]⁺ 325.1330, found 325.1335
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For minor diastereomer, er = 94:6 [t (major) = 14.5 min, t (minor) = 15.6 min]

(4aS,8R,8aS)-8-(E-2-chlorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.54 (dd, J = 7.8, 1.7 Hz, 1H), 7.29 (dd, J = 7.9, 1.4 Hz, 1H), 7.16 (td, J = 7.6, 1.4 Hz, 1H), 7.10 (td, J = 7.6, 1.7 Hz, 1H), 6.72 – 6.64 (m, 2H), 2.67 – 2.60 (m, 1H), 2.44 (d, J = 3.0 Hz, 1H), 2.33 – 2.22 (m, 2H), 2.00 – 1.85 (m, 3H), 1.79 – 1.72 (m, 1H), 1.68 – 1.62 (m, 2H), 1.61 – 1.53 (m, 2H), 1.52 – 1.44 (m, 1H), 1.24 (s, 3H), 1.12 – 1.06 (m, 1H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 212.2, 139.0, 136.0, 132.6, 129.6, 127.9, 126.9, 126.8, 124.7, 60.8, 43.4, 41.0, 40.6, 38.8, 31.8, 27.2, 27.1, 22.7, 21.5
IR (neat) νmax (cm⁻¹)	2922, 2187, 1975, 1711, 1462, 1379, 1088, 1047, 879, 696, 631, 534, 530, 507, 457
HRMS (ESI)	m/z calcd. for C₁₉H₂₃ClONa⁺ [M + Na]⁺ 325.1330, found 325.1332
Chiral SFC [Column 4, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 94:6 [t (major) = 8.0 min, t (minor) = 9.0 min]

(4aS,8S,8aS)-8-(E-2-chlorostyryl)-4a-methyloctahydronaphthalen-1(2H)-one
¹H NMR (500 MHz, CDCl₃)	δ 7.44 (dd, J = 7.7, 1.8 Hz, 1H), 7.28 (dd, J = 7.8, 1.4 Hz, 1H), 7.18 – 7.09 (m, 2H), 6.70 (d, J = 15.7 Hz, 1H), 5.89 (dd, J = 15.8, 8.8 Hz, 1H), 2.74 – 2.66 (m, 1H), 2.41 (td, J = 13.8, 7.3 Hz, 1H), 2.26 (td, J = 13.6, 5.0 Hz, 1H), 2.20 – 2.15 (m, 1H), 2.02 – 1.95 (m, 1H), 1.94 – 1.83 (m, 3H), 1.78 – 1.62 (m, 2H), 1.60 – 1.56 (m, 1H), 1.26 – 1.19 (m, 2H), 1.16 – 1.11 (m, 1H), 0.94 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 214.3, 135.5, 135.4, 132.8, 129.5, 128.4, 127.2, 126.9, 125.9, 65.0, 41.9, 39.3, 37.9, 37.6, 32.9, 29.5, 28.0, 22.5, 21.1
IR (neat) νmax (cm⁻¹)	2920, 2368, 2162, 1975, 1462, 1375, 1090, 1049, 879, 631, 554, 534, 525, 503, 492
HRMS (ESI)	m/z calcd. for C₁₉H₂₃ClONa⁺ [M + Na]⁺ 325.1330, found 325.1335
Chiral SFC [Column 1, isocratic 3 % MeOH / 97 % supercritical CO2 for 20 min, flow = 1.5 mL/min]	For major diastereomer, er = 94:6 [t (major) = 10.8 min, t (minor) = 14.0 min]

8,8-dimethyl-7-vinylbicyclo[3.2.1]octan-2-one
Diastereoisomers in NMR	Two inseparable diastereoisomers were present in NMR (dr = 1.1 : 1) of which the signals of the major diastereoisomer are marked with • and minor diastereoisomer with ◊
¹H NMR (500 MHz, CDCl₃)	δ 5.95 (ddd, J = 16.8, 10.3, 6.3 Hz, ◊ 1H), 5.79 (ddd, J = 17.1, 10.5, 5.6 Hz, • 1H), 5.13 – 5.03 (m, • 2H), 5.03 – 4.93 (m, ◊ 2H), 3.19 – 3.09 (m, • 1H), 2.75 – 2.66 (m, ◊ 1H), 2.47 – 2.36 (m, • 1H, ◊ 1H), 2.33 (d, J = 6.3 Hz, ◊ 1H), 2.26 – 2.08 (m, • 3H, ◊ 2H), 2.01 – 1.86 (m, • 1H, ◊ 4H), 1.73 – 1.63 (m, • 2H), 1.55 (dd, J = 14.0, 6.1 Hz, • 1H), 1.06 (s, • 3H), 1.04 (s, ◊ 3H), 0.96 (s, • 3H), 0.94 (s, ◊ 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ ◊ 214.0, • 213.9, ◊ 143.3, • 138.2, • 115.7, ◊ 113.8, • 67.0, ◊ 66.7, ◊ 45.5, • 45.0, ◊ 44.7, ◊ 44.1, • 42.8, • 42.3, ◊ 36.3, • 35.2, ◊ 33.5, • 32.8, • 27.9, ◊ 27.7, ◊ 27.2, • 26.6, ◊ 22.5, • 22.5
IR (neat) νmax (cm⁻¹)	2366, 2251, 2166, 1709, 770, 631, 544, 532, 525, 519, 500, 480
HRMS (ESI)	m/z calcd. for C₁₂H₁₉O⁺ [M + H]⁺ 179.1430, found 179.1426

(1R,5S,7S)-8,8-dimethyl-7-(E-styryl)bicyclo[3.2.1]octan-2-one
¹H NMR (500 MHz, CDCl₃)	δ 7.32 – 7.25 (m, 4H), 7.21 – 7.17 (m, 1H), 6.46 (dd, J = 15.9, 1.9 Hz, 1H), 6.16 (dd, J = 15.9, 6.1 Hz, 1H), 3.36 – 3.29 (m, 1H), 2.58 – 2.51 (m, 1H), 2.41 (d, J = 6.2 Hz, 1H), 2.30 – 2.16 (m, 2H), 1.98 – 1.90 (m, 2H), 1.74 – 1.68 (m, 1H), 1.64 (dd, J = 14.0, 6.0 Hz, 1H), 1.11 (s, 3H), 0.99 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 213.7, 137.3, 131.1, 130.0, 128.6, 127.4, 126.3, 66.8, 45.1, 42.9, 41.7, 35.2, 33.9, 27.9, 26.7, 22.5
IR (neat) νmax (cm⁻¹)	2920, 1697, 1493, 1464, 1447, 1414, 1367, 1325, 1242, 1159, 968, 746, 690, 515, 478
HRMS (ESI)	m/z calcd. for C₁₈H₂₃O⁺ [M + H]⁺ 255.1743, found 255.1747

(1R,5S,7R)-8,8-dimethyl-7-(E-styryl)bicyclo[3.2.1]octan-2-one
¹H NMR (500 MHz, CDCl₃)	δ 7.34 – 7.27 (m, 4H), 7.23 – 7.18 (m, 1H), 6.37 (d, J = 16.2 Hz, 1H), 6.31 (dd, J = 15.8, 6.4 Hz, 1H), 2.94 – 2.85 (m, 1H), 2.52 – 2.40 (m, 1H), 2.33 (s, 1H), 2.29 – 2.18 (m, 2H), 2.07 (dd, J = 13.7, 9.5 Hz, 1H), 2.02 – 1.93 (m, 2H), 1.76 – 1.69 (m, 1H), 1.11 (s, 3H), 0.97 (s, 3H)
¹³C NMR {¹H} (126 MHz, CDCl₃)	δ 213.8, 137.4, 135.3, 129.6, 128.7, 127.3, 126.2, 67.6, 45.5, 44.3, 44.2, 37.0, 33.5, 27.8, 27.2, 22.5
IR (neat) νmax (cm⁻¹)	2928, 2872, 1707, 1462, 1190, 1084, 1043, 962, 879, 804, 744, 692, 467
HRMS (ESI)	m/z calcd. for C₁₈H₂₃O⁺ [M + H]⁺ 255.1743, found 255.1745