Compound characterization data — Abir Das et al., 2026

Abir Das, Srilata Goswami, J. Richard Premkumar, Basker Sundararaju. “Cobalt catalyzed divergent construction of non-adjacent multiple chiral elements.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007658/v1

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3aa
Specific rotation	[α]D²⁰ = 256.14 (c = 0.24, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.62 (dd, J = 4.8, 0.9 Hz, 1H), 7.78 (td, J = 7.8, 1.9 Hz, 1H), 7.69 – 7.49 (m, 4H), 7.46 – 7.30 (m, 4H), 7.16 (td, J = 7.6, 1.6 Hz, 1H), 6.57 (dd, J = 7.8, 1.5 Hz, 1H), 4.95 (d, J = 8.2 Hz, 1H), 4.56 (d, J = 8.1 Hz, 1H), 2.05 (s, 3H), 1.36 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.70, 176.61, 161.36, 149.11, 148.01, 143.77, 138.40, 136.62, 130.42, 130.02, 129.74, 129.60, 129.15, 128.81, 127.15, 125.61, 125.43, 125.04, 114.09, 84.43, 50.43, 49.07, 35.63, 31.56, 22.31
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₆N₄O₂ is 439.2134 and found 439.2132
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 250 nm)	98 % ee; t (minor) = 30.147 min, t (major) = 32.704 min
Diastereomeric ratio	>20:1 dr
Enantiomeric excess over time (DMSO, air, 110 °C)	0 h: 97.840 %; 2 h: 97.121 %; 4 h: 96.751 %; 6 h: 96.005 %; 8 h: 95.327 %; 10 h: 94.118 %
Racemization relation	ln(ee₀/eeₜ) = 2kt
Slope of ln(ee₀/eeₜ) against time (h)	0.0036 ± 3.1234 × 10⁻⁴
C–N rotational barrier (ΔG; reported in Main)	35.9 kcal mol⁻¹
C–N rotational barrier (ΔG; reported in Main and SI)	35.39 kcal mol⁻¹
Racemization rate constant at 25 °C	1.1281 × 10⁻¹³ s⁻¹
Racemization half-life at 25 °C	1.95 × 10⁵ years

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-5,8-dimethyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ba
Specific rotation	[α]D²⁰ = 189.30 (c = 0.18, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.64 (dd, J = 4.8, 2.7 Hz, 1H), 7.80 (td, J = 7.7, 1.8 Hz, 1H), 7.58 (dd, J = 8.2, 1.4 Hz, 1H), 7.54 – 7.50 (m, 1H), 7.48 (s, 2H), 7.38 – 7.30 (m, 2H), 7.25 – 7.22 (m, 1H), 7.18 (td, J = 7.5, 1.4 Hz, 1H), 6.60 (dd, J = 7.8, 1.5 Hz, 1H), 4.93 (d, J = 8.1 Hz, 1H), 4.52 (d, J = 8.0 Hz, 1H), 2.37 (s, 3H), 2.04 (s, 3H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.88, 176.81, 161.56, 149.16, 148.12, 141.03, 139.99, 138.42, 136.82, 130.51, 130.17 (d, J = 4.0 Hz), 129.62, 128.88, 127.20, 126.10, 125.39, 124.75, 114.07, 84.25, 50.38, 49.41, 35.72, 31.63, 22.29, 21.29
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₈N₄O₂ is 453.2291, found 453.2285
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 250 nm)	98 % ee; t (minor) = 27.723 min, t (major) = 29.548 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-5-(tert-butyl)-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ca
Specific rotation	[α]D²⁰ = 297.09 (c = 0.19, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (dd, J = 4.4, 3.1 Hz, 1H), 7.88 – 7.77 (m, 1H), 7.60 – 7.52 (m, 3H), 7.41 – 7.32 (m, 2H), 7.30 (d, J = 0.9 Hz, 1H), 7.19 (td, J = 7.4, 1.3 Hz, 1H), 7.15 (s, 1H), 6.61 (dd, J = 7.8, 1.6 Hz, 1H), 4.93 (d, J = 8.0 Hz, 1H), 4.48 – 4.41 (m, 1H), 2.03 (s, 3H), 1.36 (s, 9H), 1.33 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.07, 175.93, 175.68, 160.74, 152.00, 148.60, 147.44, 141.29, 137.83, 129.94, 129.43, 129.02, 128.22, 127.91, 126.61, 124.92, 118.97, 114.04, 107.65, 83.84, 55.51, 49.16, 49.00, 38.35, 35.08, 31.00, 26.44, 21.66
ESI-MS	[M+H]⁺ calculated for C₃₁H₃₄N₄O₂ is 495.2960, found 495.2955
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 250 nm)	98 % ee; t (minor) = 21.838 min, t (major) = 23.520 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-5-methoxy-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3da
Specific rotation	[α]D²⁰ = 320.05 (c = 0.23, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (dd, J = 4.8, 1.7 Hz, 1H), 7.82 (td, J = 7.7, 1.9 Hz, 1H), 7.62 – 7.47 (m, 3H), 7.36 (td, J = 8.0, 3.0 Hz, 2H), 7.23 – 7.16 (m, 2H), 6.98 (dd, J = 8.6, 2.5 Hz, 1H), 6.61 (dd, J = 7.8, 1.5 Hz, 1H), 4.94 (d, J = 8.0 Hz, 1H), 4.51 (d, J = 8.1 Hz, 1H), 3.80 (s, 3H), 2.02 (s, 3H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.93, 176.80, 161.61, 161.22, 149.21, 148.18, 138.40 (d, J = 23.4 Hz), 135.88, 130.57, 130.14, 129.74, 128.96, 127.31, 125.85, 125.45, 116.75, 114.18, 109.43, 83.99, 55.51, 50.46, 49.59, 35.78, 31.68, 27.08, 22.35
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₈N₄O₃ is 469.2240, found 649.2240
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	>99 % ee; t (major) = 66.818 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-5-(benzyloxy)-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ea
Specific rotation	[α]D²⁰ = 460.36 (c = 0.58, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (dd, J = 4.8, 2.8 Hz, 1H), 7.81 (td, J = 7.8, 1.8 Hz, 1H), 7.60 (dd, J = 8.1, 1.4 Hz, 1H), 7.53 (dd, J = 8.3, 7.6 Hz, 2H), 7.46 – 7.38 (m, 2H), 7.42 – 7.32 (m, 4H), 7.33 – 7.28 (m, 2H), 7.21 (td, J = 7.5, 1.4 Hz, 1H), 7.07 (dd, J = 8.1, 2.9 Hz, 1H), 6.62 (dd, J = 7.8, 1.5 Hz, 1H), 5.13 – 5.02 (m, 2H), 4.97 (d, J = 8.1 Hz, 1H), 4.53 (d, J = 8.1 Hz, 1H), 2.04 (s, 3H), 1.39 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.81, 176.64, 161.53, 160.31, 149.15, 148.10, 138.42, 138.24, 136.40, 136.09, 130.52, 130.10, 129.65, 128.87, 128.49, 127.97, 127.47, 127.22, 125.87, 125.38, 117.33, 114.10, 110.41, 83.91, 70.15, 50.39, 49.54, 35.70, 31.62, 22.28
ESI-MS	[M+H]⁺ calculated for C₄₆H₃₃N₃O₄ is 545.2553, found 545.2446
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	>99 % ee; t (major) = 23.284 min
Diastereomeric ratio	20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-5-(methylthio)-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3fa
Specific rotation	[α]D²⁰ = 469.65 (c = 0.7, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 – 8.60 (m, 1H), 7.87 – 7.75 (m, 1H), 7.58 (d, J = 8.1 Hz, 3H), 7.56 – 7.45 (m, 1H), 7.38 – 7.33 (m, 2H), 7.31 – 7.28 (m, 1H), 7.19 (t, J = 7.5 Hz, 1H), 6.60 (dd, J = 7.8, 1.6 Hz, 1H), 4.93 (d, J = 8.1 Hz, 1H), 4.52 (d, J = 8.2 Hz, 1H), 2.46 (s, 3H), 2.02 (s, 3H), 1.36 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.63, 176.48, 161.44, 149.16, 148.06, 141.16, 140.40, 138.46, 137.54, 130.49, 130.01, 129.68, 128.87, 127.34, 127.23, 125.47, 125.17, 122.28, 114.17, 84.13, 50.29, 49.27, 35.68, 31.60, 27.11, 22.18, 15.33
ESI-MS	[M+H]⁺ calculated for C₄₅H₃₁N₃O₃S is 485.2011, found 485.2001
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	>99 % ee; t (major) = 11.568 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-5-phenyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ga
Specific rotation	[α]D²⁰ = 319.87 (c = 0.22, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 (dd, J = 4.9, 1.8 Hz, 1H), 7.91 (s, 1H), 7.85 (td, J = 7.8, 1.9 Hz, 1H), 7.68 (s, 2H), 7.62 – 7.58 (m, 4H), 7.40 (dt, J = 24.2, 7.1 Hz, H), 7.20 (td, J = 7.7, 1.6 Hz, 1H), 6.64 (dd, J = 8.0, 1.6 Hz, 1H), 4.99 (d, J = 8.2 Hz, 1H), 4.62 (d, J = 8.2 Hz, 1H), 2.10 (s, 3H), 1.40 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.82, 176.72, 161.46, 149.19, 148.14, 143.18, 142.83, 140.18, 138.62, 137.41, 130.58, 130.10, 129.75, 128.96, 128.78, 128.41, 127.67, 127.26 (d, J = 6.4 Hz), 125.60, 125.42, 124.29, 114.38, 84.40, 50.51, 49.47, 35.77, 31.68, 27.06, 22.44
ESI-MS	[M+H]⁺ calculated for C₃₃H₃₁N₄O₂ is 515.2447, found 515.2442
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	>99 % ee; t (major) = 41.640 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-5-cyclohexyl-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ha
Specific rotation	[α]D²⁰ = 217.18 (c = 0.57, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.68 – 8.60 (m, 1H), 7.79 (td, J = 7.7, 1.9 Hz, 1H), 7.63 – 7.47 (m, 4H), 7.40 – 7.29 (m, 2H), 7.31 – 7.23 (m, 1H), 7.20 – 7.15 (m, 1H), 6.63 – 6.60 (m, 1H), 4.95 (d, J = 9.3 Hz, 1H), 4.53 (d, J = 8.3 Hz, 1H), 2.61 – 2.47 (m, 1H), 2.03 (s, 3H), 1.92 – 1.77 (m, 6H), 1.72 (d, J = 11.9 Hz, 1H), 1.40 – 1.39 (m, 2H), 1.38 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.89, 176.85, 161.48, 150.14, 149.10, 148.10, 141.34, 138.44, 136.68, 130.51, 130.13, 129.59, 128.84, 128.07, 127.17, 125.38, 124.73, 123.86, 114.18, 84.29, 50.46, 49.43, 44.36, 35.70, 34.44, 34.09, 31.61, 27.07, 26.67 (d, J = 2.4 Hz), 25.93, 22.43
ESI-MS	[M+H]⁺ calculated for C₃₃H₃₇N₄O₂ is 521.1917, found 521.1917
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 14.119 min, t (major) = 10.478 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-5-fluoro-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ia
Specific rotation	[α]D²⁰ = 376.29 (c = 0.39, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 (d, J = 4.8 Hz, 1H), 7.85 (t, J = 7.8 Hz, 1H), 7.61 – 7.53 (m, 3H), 7.38 (dt, J = 16.3, 6.3 Hz, 3H), 7.20 (t, J = 7.5 Hz, 1H), 7.13 (td, J = 8.8, 2.3 Hz, 1H), 6.60 (d, J = 7.6 Hz, 1H), 4.95 (d, J = 8.0 Hz, 1H), 4.52 (d, J = 8.0 Hz, 1H), 2.02 (s, 3H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.50, 176.18, 165.09, 162.61, 161.39, 149.29, 148.12, 139.53, 138.85 (d, J = 9.2 Hz), 138.60, 130.49, 129.98, 129.83, 129.00, 127.33, 126.55 (d, J = 9.4 Hz), 125.65, 116.85 (d, J = 23.0 Hz), 114.48, 112.74 (d, J = 23.5 Hz), 83.85, 50.23, 49.53, 35.77, 31.68, 27.09, 22.48
¹⁹F NMR (376 MHz, chloroform-d)	δ −111.18
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₆FN₄O₂ is 457.2040, found 457.2043
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	97 % ee; t (minor) = 15.840, t (major) = 13.711 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-5-chloro-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ja
Specific rotation	[α]D²⁰ = 487.87 (c = 0.38, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.66 (d, J = 4.7 Hz, 1H), 7.84 (t, J = 7.8 Hz, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.69 – 7.50 (m, 2H), 7.45 – 7.30 (m, 3H), 7.20 (t, J = 7.5 Hz, 1H), 6.79 (t, J = 6.2 Hz, 1H), 6.61 (d, J = 7.6 Hz, 1H), 4.95 (d, J = 7.9 Hz, 1H), 4.52 (d, J = 8.3 Hz, 1H), 2.03 (s, 3H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.50, 176.18, 165.09, 162.61, 161.39, 149.29, 148.12, 139.53, 138.85 (d, J = 9.2 Hz), 138.60, 130.49, 129.98, 129.83, 129.00, 127.33, 126.55 (d, J = 9.4 Hz), 125.65, 116.85 (d, J = 23.0 Hz), 114.48, 112.74 (d, J = 23.5 Hz), 83.85, 50.23, 49.53, 35.77, 31.68, 27.09, 22.48
ESI-MS	[M+H]⁺ calculated for C₂₆H₂₇ClN₄O₂ is 473.1744, found 473.1741
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 22.489 min, t (major) = 24.908 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-5-bromo-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ka
Specific rotation	[α]D²⁰ = 232.40 (c = 0.1, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (dd, J = 4.9, 2.7 Hz, 1H), 7.88 – 7.78 (m, 2H), 7.63 – 7.49 (m, 3H), 7.48 (dd, J = 8.5, 3.9 Hz, 1H), 7.43 – 7.31 (m, 2H), 7.20 (td, J = 7.5, 1.4 Hz, 1H), 6.61 (dd, J = 7.8, 1.5 Hz, 1H), 4.93 (d, J = 8.2 Hz, 1H), 4.52 (d, J = 8.2 Hz, 1H), 2.02 (s, 3H), 1.36 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.29, 175.98, 161.35, 149.29, 148.06, 142.85, 138.71, 138.50, 132.56, 130.47, 129.92, 129.77, 128.89 (d, J = 11.8 Hz), 127.27, 126.59, 125.63, 123.89, 114.39, 84.05, 50.13, 49.19, 35.71, 31.63, 22.25
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₆BrN₄O₂ is 517.1239, found 517.1231
Chiral HPLC (Daicel Chiralpak IF; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	>99 % ee; t (minor) = 11.678 min, t (major) = 9.765 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-5-(trifluoromethyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3la
Specific rotation	[α]D²⁰ = 397.10 (c = 0.41, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 (d, J = 4.8 Hz, 1H), 7.96 (s, 1H), 7.86 (t, J = 7.7 Hz, 1H), 7.73 (q, J = 8.2 Hz, 2H), 7.59 (t, J = 9.4 Hz, 2H), 7.39 (dt, J = 15.2, 6.8 Hz, 2H), 7.21 (t, J = 7.5 Hz, 1H), 6.61 (d, J = 7.7 Hz, 1H), 4.99 (d, J = 8.3 Hz, 1H), 4.60 (d, J = 8.4 Hz, 1H), 2.07 (s, 3H), 1.38 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.18, 175.95, 161.26, 149.39, 148.10, 147.64, 138.62, 137.54, 130.48, 129.89, 129.05, 127.36, 126.53 (d, J = 3.9 Hz), 125.85, 122.94 (d, J = 4.5 Hz), 114.67, 84.34, 50.33, 49.22, 35.78, 31.69, 27.09, 22.50
¹⁹F NMR (376 MHz, chloroform-d)	δ −62.25
ESI-MS	[M+H]⁺ calculated for C₃₉H₂₆ClN₃O₃S is 652.1462, found 652.1446
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 15.433 min, t (major) = 18.120 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-5-(trifluoromethoxy)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ma
Specific rotation	[α]D²⁰ = 290.56 (c = 0.19, CHCl₃)
¹H NMR (400 MHz, CDCl₃)	δ 8.67 (dd, J = 4.8, 2.7 Hz, 1H), 7.91 – 7.80 (m, 1H), 7.66 – 7.49 (m, 4H), 7.45 – 7.32 (m, 2H), 7.29 (dd, J = 7.5, 2.2 Hz, 1H), 7.21 (td, J = 7.5, 1.4 Hz, 1H), 6.62 (dd, J = 7.8, 1.5 Hz, 1H), 4.99 (d, J = 8.3 Hz, 1H), 4.55 (d, J = 8.3 Hz, 1H), 2.03 (s, 3H), 1.37 (s, 9H)
¹³C NMR (101 MHz, chloroform-d)	δ 176.30, 175.98, 161.30, 150.42, 149.34, 148.09, 142.36, 138.59, 130.48, 129.86, 129.01, 127.35, 126.46, 125.73, 122.15, 118.22, 114.63, 83.95, 50.22, 49.35, 35.75, 31.66, 27.13, 22.56
¹⁹F NMR (376 MHz, chloroform-d)	δ −57.66
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₆F₃N₄O₃ is 523.1957, found 523.1951
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 10.895 min, t (major) = 13.842 min
Diastereomeric ratio	>20:1 dr

methyl (S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-1,3-dioxo-8-((E)-pyridin-2-yldiazenyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole-5-carboxylate
Identifier	3na
Specific rotation	[α]D²⁰ = 324.08 (c = 1.06, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.66 (d, J = 5.0 Hz, 1H), 8.34 (s, 1H), 8.13 (d, J = 8.2 Hz, 1H), 7.84 (t, J = 7.8 Hz, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.63 – 7.50 (m, 2H), 7.38 (dt, J = 15.6, 7.7 Hz, 2H), 7.18 (t, J = 7.5 Hz, 1H), 6.57 (d, J = 7.8 Hz, 1H), 4.96 (d, J = 8.2 Hz, 1H), 4.58 (d, J = 8.3 Hz, 1H), 3.90 (s, 3H), 2.06 (s, 3H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.36, 176.16, 166.28, 161.31, 149.32, 148.54, 138.59, 137.14, 131.96, 130.82, 130.47, 129.95, 129.80, 128.98, 127.29, 127.04, 125.74, 125.25, 114.55, 84.41, 67.01, 52.27, 50.25, 49.32, 35.75, 31.66, 27.11, 22.35
ESI-MS	[M+H]⁺ calculated for C₂₉H₂₉N₄O₄ is 497.2189, found 497.2181
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	97 % ee; t (minor) = 20.788 min, t (major) = 27.112 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-6,8-dimethyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3oa
Specific rotation	[α]D²⁰ = 298.71 (c = 0.48, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.64 (d, J = 4.8 Hz, 1H), 7.81 (t, J = 7.8 Hz, 1H), 7.56 (t, J = 9.3 Hz, 3H), 7.45 – 7.34 (m, 3H), 7.24 – 7.09 (m, 2H), 6.58 (d, J = 7.8 Hz, 1H), 4.92 (d, J = 8.0 Hz, 1H), 4.52 (d, J = 8.1 Hz, 1H), 2.40 (s, 3H), 2.04 (s, 3H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.87, 176.85, 161.48, 149.14, 148.10, 143.91, 139.22, 138.45, 133.86, 130.81, 130.49, 130.14, 129.61, 128.85, 127.18, 125.43, 125.32, 114.30, 84.44, 50.16, 49.49, 35.69, 31.62, 27.10, 22.25, 21.36
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₉N₄O₂ is 453.2291, found 453.2291
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 30.566 min, t (major) = 32.181 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-6-bromo-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3pa
Specific rotation	[α]D²⁰ = 261.96 (c = 0.29, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.63 (dd, J = 4.8, 2.1 Hz, 1H), 7.85 – 7.75 (m, 1H), 7.62 – 7.46 (m, 4H), 7.41 – 7.29 (m, 2H), 7.25 (d, J = 10.5 Hz, 1H), 7.18 (t, J = 8.2 Hz, 1H), 6.60 (dd, J = 7.8, 1.5 Hz, 1H), 4.95 (d, J = 8.2 Hz, 1H), 4.53 (d, J = 8.2 Hz, 1H), 2.04 (s, 3H), 1.38 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.88, 176.84, 161.46, 149.08, 148.10, 145.00, 141.18, 138.46 (d, J = 2.4 Hz), 136.71, 130.48, 130.14 (d, J = 3.0 Hz), 129.60, 128.85, 127.18, 125.39, 124.71, 114.16, 84.27, 50.40, 49.43, 35.69, 35.38, 33.38, 31.61, 27.06, 22.36, 22.23, 13.79
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₆BrN₄O₂ is 517.1239, found 517.1237
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 18.426 min, t (major) = 21.918 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-6-(trifluoromethyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3qa
Specific rotation	[α]D²⁰ = 299.56 (c = 0.28, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.66 (dd, J = 4.8, 2.7 Hz, 1H), 8.04 (d, J = 1.2 Hz, 1H), 7.91 – 7.78 (m, 2H), 7.72 – 7.66 (m, 1H), 7.61 – 7.54 (m, 2H), 7.52 – 7.44 (m, 1H), 7.44 – 7.31 (m, 1H), 7.19 (td, J = 7.5, 1.4 Hz, 1H), 6.59 (dd, J = 7.8, 1.5 Hz, 1H), 5.01 (d, J = 8.3 Hz, 1H), 4.59 (d, J = 8.3 Hz, 1H), 2.07 (s, 3H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.15, 175.83, 161.20, 156.90, 149.29, 148.07, 146.01, 144.79, 140.63, 139.62, 138.85, 138.59, 130.47, 129.86 (d, J = 5.7 Hz), 128.97, 128.74 (d, J = 4.8 Hz), 127.29, 126.33, 125.77, 115.67, 114.71, 108.23, 84.29, 50.39, 48.96, 35.72, 31.63, 27.19, 22.41, 12.58
¹⁹F NMR (471 MHz, chloroform-d)	δ −62.54
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₆F₃N₄O₂ is 507.2008, found 507.2007
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 12.347 min, t (major) = 10.199 min
Diastereomeric ratio	>20:1 dr

(S,3aR,10R,10aS)-2-(2-(tert-butyl)phenyl)-10-methyl-10-((E)-pyridin-2-yldiazenyl)-10,10a-dihydrobenzo[5,6]indeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ra
Specific rotation	[α]D²⁰ = 436.72 (c = 0.39, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (dd, J = 4.9, 2.8 Hz, 1H), 8.16 (d, J = 1.3 Hz, 1H), 8.10 (s, 1H), 7.97 – 7.88 (m, 1H), 7.91 – 7.83 (m, 1H), 7.79 (td, J = 7.7, 1.8 Hz, 1H), 7.59 (dd, J = 8.2, 1.4 Hz, 1H), 7.54 (dt, J = 8.0, 1.0 Hz, 1H), 7.52 – 7.47 (m, 2H), 7.39 – 7.29 (m, 2H), 7.14 (td, J = 7.6, 1.5 Hz, 1H), 6.52 (dd, J = 7.9, 1.5 Hz, 1H), 4.99 (d, J = 8.1 Hz, 1H), 4.73 (d, J = 9.6 Hz, 0H), 2.22 (s, 3H), 1.41 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.83, 176.64, 161.47, 149.19, 148.12, 141.86, 138.47, 134.76, 134.25, 133.84, 130.49, 130.14, 129.66, 128.88, 128.18 (d, J = 4.2 Hz), 127.22, 126.57, 126.35, 125.48, 124.85, 124.59, 114.35, 84.05, 49.95, 49.88 35.74, 31.67, 27.12, 22.24
ESI-MS	[M+H]⁺ calculated for C₃₁H₂₉N₄O₂ is 489.2291, found 489.2287
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	94 % ee; t (minor) = 15.547 min, t (major) = 13.452 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-5-bromo-2-(2-(tert-butyl)phenyl)-8-ethyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3sa
Specific rotation	[α]D²⁰ = 215.12 (c = 0.24, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 (dd, J = 4.8, 2.6 Hz, 1H), 7.87 – 7.79 (m, 2H), 7.62 – 7.57 (m, 2H), 7.56 – 7.45 (m, 2H), 7.44 – 7.31 (m, 2H), 7.20 (td, J = 7.6, 1.4 Hz, 1H), 6.59 (dd, J = 7.8, 1.5 Hz, 2H), 4.99 (d, J = 7.9 Hz, 1H), 4.44 (d, J = 7.9 Hz, 1H), 3.07 – 2.68 (m, 1H), 2.59 – 2.43 (m, 1H), 1.37 (s, 9H), 1.00 (t, J = 7.3 Hz, 3H)
¹³C NMR (101 MHz, chloroform-d)	δ 176.67, 175.89, 161.41, 149.34, 148.18, 141.80, 141.46, 139.46, 138.58, 132.42 (d, J = 2.7 Hz), 130.28, 130.05, 129.80, 128.96 (d, J = 8.1 Hz), 128.26, 127.34, 127.06, 125.65, 123.97, 113.90, 88.52, 49.96, 47.63, 35.80, 31.73, 29.68, 26.96, 9.53
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₈BrN₄O₂ is 531.1396, found 531.1390
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 8.761 min, t (major) = 11.057 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-8-butyl-2-(2-(tert-butyl)phenyl)-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ta
Specific rotation	[α]D²⁰ = 479.15 (c = 0.44, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.66 (d, J = 4.8 Hz, 1H), 7.82 (td, J = 7.8, 1.9 Hz, 1H), 7.67 (dd, J = 12.9, 7.5 Hz, 2H), 7.58 (d, J = 8.4 Hz, 1H), 7.51 (d, J = 8.1 Hz, 1H), 7.50 – 7.30 (m, 4H), 7.17 (t, J = 7.6 Hz, 1H), 6.60 – 6.51 (m, 1H), 5.00 (d, J = 7.9 Hz, 1H), 4.47 (d, J = 7.9 Hz, 1H), 2.83 – 2.69 (m, 1H), 2.60 – 2.41 (m, 1H), 1.53 – 1.49 (m, 2H), 1.38 (s, 9H), 1.16 – 1.00 (m, 2H), 0.87 (t, J = 7.2 Hz, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 177.09, 176.61, 161.55, 149.23, 148.22, 142.58, 138.51, 137.39, 130.30 (d, J = 3.7 Hz), 129.80, 129.69, 129.02, 128.94, 127.24, 125.69, 125.58, 125.45, 113.75, 88.60, 50.30, 47.76, 35.77, 33.84, 31.72, 27.22, 23.10, 13.89
ESI-MS	[M+H]⁺ calculated for C₃₀H₃₃N₄O₂ is 481.2604, found 481.2602
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 13.860 min, t (major) = 12.022 min
Diastereomeric ratio	>20:1 dr
Single-crystal XRD, formula and formula weight	C₃₁H₃₄Cl₂N₄O₂; Mᵣ = 445.86 g mol⁻¹
Single-crystal XRD, asymmetric unit	One molecule of 3ta and one DCM (solvent) molecule
Single-crystal XRD, crystal colour and size	Clear light yellow; 0.2 × 0.1 × 0.1 mm
Single-crystal XRD, crystal system and space group	Trigonal, P3₂
Single-crystal XRD, unit cell	a = 10.6020(3) Å, b = 10.6020(3) Å, c = 22.2165(8) Å; α = 90°, β = 90°, γ = 120°; V = 2162.63(15) Å³; Z = 4; Dcalc = 1.369 g cm⁻³
Single-crystal XRD, data collection	T = 273.15 K; λ = 0.71073 Å; μ(Mo-Kα) = 0.218 mm⁻¹; empirical absorption correction (Tₘᵢₙ = 0.6666, Tₘₐₓ = 0.7457); CCD Bruker APEX-II diffractometer; 2.750 < θ < 28.304
Single-crystal XRD, reflections	47606 measured; 7152 independent; 6589 with I > 2σ(I)
Single-crystal XRD, refinement	Structures were solved by direct methods and refined (SHELXL-97) by full matrix least squares based on F² to R₁ = 0.0343 [I > 2σ(I)], wR₂ = 0.0813; 356 parameters; H atoms riding; S = 1.025; residual electron density +0.236 / −0.356 e Å⁻³
Single-crystal XRD, CCDC deposition number	2575178

(S,3aR,8R,8aS)-8-benzyl-2-(2-(tert-butyl)phenyl)-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ua
Specific rotation	[α]D²⁰ = 337.23 (c = 0.25, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (dd, J = 4.6, 1.8 Hz, 1H), 7.82 (td, J = 7.7, 1.9 Hz, 1H), 7.68 (d, J = 7.3 Hz, 1H), 7.53 (td, J = 8.7, 1.6 Hz, 2H), 7.48 – 7.42 (m, 3H), 7.41 – 7.36 (m, 2H), 7.32 (td, J = 7.7, 1.5 Hz, 1H), 7.16 (dt, J = 7.3, 3.4 Hz, 5H), 7.09 (td, J = 7.6, 1.4 Hz, 1H), 5.99 (dd, J = 7.8, 1.5 Hz, 1H), 5.00 (d, J = 8.1 Hz, 1H), 4.50 (d, J = 8.1 Hz, 1H), 4.24 (d, J = 14.4 Hz, 1H), 3.77 (d, J = 14.5 Hz, 1H), 1.35 (s, 9H)
¹³C NMR (101 MHz, chloroform-d)	δ 176.61, 176.28, 161.46, 149.23, 147.95, 142.51, 138.52, 137.27, 135.97, 131.28, 130.63, 130.05 (d, J = 7.4 Hz), 129.62, 128.83, 128.67, 128.06, 127.08, 126.58, 126.38, 125.91, 125.56, 113.44, 87.25, 50.52, 48.70, 40.71, 35.67, 31.67, 27.09
ESI-MS	[M+H]⁺ calculated for C₃₃H₃₁N₄O₂ is 515.2247, found 515.2238
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 22.457 min, t (major) = 25.197 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-5-(thiophen-2-yl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3va
Specific rotation	[α]D²⁰ = 279.66 (c = 1.3, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 (dd, J = 4.8, 1.6 Hz, 1H), 7.91 (d, J = 1.6 Hz, 1H), 7.87 – 7.81 (m, 1H), 7.68 (dd, J = 8.2, 1.6 Hz, 1H), 7.65 – 7.55 (m, 3H), 7.42 – 7.33 (m, 3H), 7.30 – 7.28 (m, 1H), 7.20 (dd, J = 8.3, 6.9 Hz, 1H), 7.11 – 7.02 (m, 1H), 6.93 – 6.48 (m, 1H), 4.98 (d, J = 9.1 Hz, 1H), 4.58 (d, J = 8.1 Hz, 1H), 1.38 (s, 9H)
¹³C NMR (125 MHz, chloroform-d)	δ 176.77, 176.63, 161.53, 149.32, 148.15, 143.31, 142.90, 138.55, 137.62, 136.30, 130.59, 130.09, 129.80, 128.98, 128.12, 127.35, 127.21, 125.61 (d, J = 3.4 Hz), 125.50, 123.88, 122.86, 114.35, 84.36, 50.42, 49.39, 35.80, 31.70, 22.33
ESI-MS	[M+H]⁺ calculated for C₃₁H₂₉N₄O₂S is 521.2011, found 830.2087
Chiral HPLC (Daicel Chiralpak IF; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 25.870 min, t (major) = 16.712 min
Diastereomeric ratio	>20:1 dr

(2R,5S)-2-isopropyl-5-methylcyclohexyl (S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-8-methyl-1,3-dioxo-8-((E)-pyridin-2-yldiazenyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole-5-carboxylate
Identifier	3wa
Specific rotation	[α]D²⁰ = 274.41 (c = 0.12, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.66 (d, J = 4.8 Hz, 1H), 8.31 (d, J = 6.6 Hz, 1H), 8.14 (t, J = 8.2 Hz, 1H), 7.84 (dt, J = 7.6, 4.5 Hz, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.61 – 7.59 (m, 2H), 7.41 – 7.35 (m, 2H), 7.22 – 7.16 (m, 1H), 6.65 – 6.52 (m, 1H), 4.95 (dd, J = 21.2, 9.3 Hz, 4H), 4.64 – 4.59 (m, 1H), 1.95 – 1.85 (m, 3H), 1.74 – 1.69 (m, 4H), 1.38 (s, 9H), 1.15 – 1.08 (m, 3H), 0.92 – 0.89 (m, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.43, 165.30, 161.39, 149.32, 148.17, 138.61, 137.07, 132.74, 131.17, 130.95, 130.52, 130.33, 130.01, 129.85, 129.04, 127.35, 127.12, 126.95, 125.73, 125.20, 123.33, 114.44, 84.44, 75.22, 50.31, 47.10, 35.79, 34.24, 29.67, 27.10, 26.45, 23.46, 21.98, 20.75, 16.36
ESI-MS	[M+H]⁺ calculated for C₂₈H₄₅N₄O₄ is 621.3441, found 621.3435
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 28.445 min, t (major) = 47.957 min
Diastereomeric ratio	>20:1 dr

2-isopropyl-5-methylphenyl (3aR,8R,8aS)-8-benzyl-2-(2-(tert-butyl)phenyl)-1,3-dioxo-8-((E)-pyridin-2-yldiazenyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole-5-carboxylate
Identifier	3xa
Specific rotation	[α]D²⁰ = 411.21 (c = 0.66, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.59 (d, J = 5.0 Hz, 1H), 8.45 (s, 1H), 8.14 (d, J = 8.3 Hz, 1H), 7.86 (s, 1H), 7.77 (t, J = 7.7 Hz, 1H), 7.68 (s, 1H), 7.39 (d, J = 8.5 Hz, 1H), 7.19 – 7.11 (m, 2H), 6.98 (t, J = 7.4 Hz, 1H), 6.85 (d, J = 27.0 Hz, 2H), 6.77 – 6.72 (m, 1H), 6.56 (d, J = 7.8 Hz, 1H), 4.95 (d, J = 8.3 Hz, 1H), 4.57 (d, J = 8.4 Hz, 1H), 2.96 (dt, J = 17.6, 7.0 Hz, 1H), 2.26 (s, 3H), 2.23 (s, 6H), 2.02 (s, 3H), 1.30 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.28, 176.08, 165.08, 164.59, 161.31, 156.57, 149.36, 149.24, 148.09 (d, J = 1.9 Hz), 143.49, 142.03, 138.64, 138.58, 137.38, 137.08, 136.59, 131.44, 131.33, 130.48, 130.16, 129.89 (d, J = 9.5 Hz), 129.03, 128.84, 127.61, 127.28 (d, J = 8.0 Hz), 127.12, 126.43, 125.66, 122.82, 122.65, 116.12, 114.52, 108.10, 84.43, 50.31, 49.27, 35.76, 31.66, 27.25, 22.98 (d, J = 4.2 Hz), 20.80, 12.27
ESI-MS	[M+H]⁺ calculated for C₃₈H₃₉N₄O₄ is 615.2971, found 615.2971
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	97 % ee; t (minor) = 22.241 min, t (major) = 36.321 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)phenyl)-6-methoxy-8-methyl-1,3-dioxo-8-((E)-pyridin-2-yldiazenyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrol-5-yl pivalate
Identifier	3ya
Specific rotation	[α]D²⁰ = 307.12 (c = 0.4, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 (d, J = 4.8 Hz, 1H), 7.89 – 7.81 (m, 1H), 7.56 (dd, J = 13.2, 8.0 Hz, 2H), 7.44 – 7.31 (m, 2H), 7.30 (s, 1H), 7.20 (t, J = 7.5 Hz, 1H), 7.15 (s, 1H), 6.62 (d, J = 7.7 Hz, 1H), 4.93 (d, J = 8.0 Hz, 1H), 4.46 (d, J = 8.1 Hz, 1H), 3.86 (s, 3H), 2.04 (s, 3H), 1.36 (s, 9H), 1.34 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.76, 176.62, 176.37, 161.44, 152.68, 149.31, 148.13, 141.97, 138.50, 130.63, 130.10, 129.71, 128.91, 128.60, 127.30, 125.58, 119.66, 114.74, 108.32, 84.53, 56.21, 49.76 (d, J = 15.9 Hz), 39.03, 35.77, 31.68, 27.12, 22.33
ESI-MS	[M+H]⁺ calculated for C₃₃H₃₇N₄O₅ is 569.2764, found 569.2761
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm; reported in SI)	>99 % ee; t (major) = 23.793 min
Enantiomeric excess reported in Main	97 % ee
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-(tert-butyl)-4-chlorophenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ab
Specific rotation	[α]D²⁰ = 379.13 (c = 0.39, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (dd, J = 4.7, 1.0 Hz, 1H), 7.86 – 7.76 (m, 1H), 7.70 – 7.58 (m, 2H), 7.53 (d, J = 8.2 Hz, 2H), 7.42 (t, J = 7.1 Hz, 2H), 7.39 – 7.35 (m, 1H), 7.15 (dd, J = 10.2, 1.8 Hz, 1H), 6.53 (dd, J = 8.3, 1.2 Hz, 1H), 4.95 (d, J = 8.2 Hz, 1H), 4.55 (d, J = 8.1 Hz, 1H), 2.04 (s, 3H), 1.35 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.60, 176.46, 161.47, 150.23, 149.23, 143.80, 138.47, 136.53, 135.62, 131.94, 129.88, 129.29 (d, J = 4.5 Hz), 128.80, 127.40, 125.67, 125.52, 125.15, 114.17, 84.50, 50.49, 49.14, 35.92, 31.41, 22.31
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₆ClN₄O₂ is 473.1744, found 473.1741
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	96 % ee; t (minor) = 16.780 min, t (major) = 20.706 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(4-bromo-2-(tert-butyl)phenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ac
Specific rotation	[α]D²⁰ = 410.32 (c = 0.39, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.66 (d, J = 4.8 Hz, 1H), 7.83 (t, J = 7.9 Hz, 1H), 7.70 (s, 1H), 7.64 (dd, J = 15.9, 7.4 Hz, 2H), 7.54 (d, J = 8.1 Hz, 1H), 7.48 – 7.37 (m, 3H), 7.34 – 7.30 (m, 1H), 6.46 (d, J = 8.3 Hz, 1H), 4.95 (d, J = 8.1 Hz, 1H), 4.55 (d, J = 8.2 Hz, 1H), 2.04 (s, 3H), 1.36 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.58, 176.44, 161.48, 150.54, 149.24, 143.82, 138.53, 136.55, 132.25 (d, J = 5.8 Hz), 130.46, 129.92, 129.35, 125.64 (d, J = 14.9 Hz), 125.19, 124.05, 114.24, 84.54, 50.53, 49.19, 35.95, 31.46, 27.10, 22.33
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₆BrN₄O₂ is 517.1239, found 517.1235
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 19.810 min, t (major) = 26.166 min
Diastereomeric ratio	>20:1 dr
Single-crystal XRD, formula and formula weight	C₂₇H₂₅BrN₄O₂; Mᵣ = 517.42 g mol⁻¹
Single-crystal XRD, crystal colour and size	Light yellow; 0.2 × 0.1 × 0.1 mm
Single-crystal XRD, crystal system and space group	Orthorhombic, P2₁2₁2₁
Single-crystal XRD, unit cell	a = 9.2889(5) Å, b = 15.4923(9) Å, c = 17.0728(8) Å; α = 90°, β = 90°, γ = 90°; V = 2456.9(2) Å³; Z = 4; Dcalc = 1.399 g cm⁻³
Single-crystal XRD, data collection	T = 273.15 K; λ = 0.71073 Å; μ(Mo-Kα) = 1.705 mm⁻¹; empirical absorption correction (Tₘᵢₙ = 0.6308, Tₘₐₓ = 0.7457); CCD Bruker APEX-II diffractometer; 2.629 < θ < 28.314
Single-crystal XRD, reflections	40218 measured; 6098 independent; 5267 with I > 2σ(I)
Single-crystal XRD, refinement	Structures were solved by direct methods and refined (SHELXL-97) by full matrix least squares based on F² to R₁ = 0.0346 [I > 2σ(I)], wR₂ = 0.0753; 311 parameters; H atoms riding; S = 1.028; residual electron density +0.464 / −0.473 e Å⁻³
Single-crystal XRD, CCDC deposition number	2575192

(S,3aR,8R,8aS)-2-(2-(tert-butyl)-4-iodophenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ad
Specific rotation	[α]D²⁰ = 219.35 (c = 0.36, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (d, J = 4.8 Hz, 1H), 7.92 – 7.79 (m, 2H), 7.64 (dd, J = 16.0, 7.4 Hz, 2H), 7.55 – 7.36 (m, 4H), 6.63 (d, J = 9.2 Hz, 1H), 6.33 – 6.28 (m, 1H), 4.94 (d, J = 8.1 Hz, 1H), 4.55 (d, J = 8.0 Hz, 1H), 2.04 (s, 1H), 1.35 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.70, 176.57, 161.61, 150.75, 149.36, 143.96, 142.38, 138.59 (d, J = 21.6 Hz), 136.67 (d, J = 5.9 Hz), 132.47, 130.06, 129.70, 129.49, 128.67, 128.42, 125.87, 125.72, 125.33, 120.23, 114.40, 108.00, 96.44, 84.69, 50.69, 49.36, 35.96, 31.62, 29.79, 27.24, 22.49
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₆IN₄O₂ is 565.1100, found 565.1105
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 19.065 min, t (major) = 27.010 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(3-(tert-butyl)-[1,1′-biphenyl]-4-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ae
Specific rotation	[α]D²⁰ = 432.01 (c = 0.48, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.67 (dd, J = 4.6, 1.8 Hz, 1H), 7.84 (td, J = 7.7, 1.9 Hz, 1H), 7.77 (d, J = 2.2 Hz, 1H), 7.74 – 7.68 (m, 1H), 7.68 – 7.60 (m, 1H), 7.61 – 7.50 (m, 3H), 7.49 – 7.33 (m, 7H), 6.68 (d, J = 8.1 Hz, 1H), 4.99 (d, J = 8.1 Hz, 1H), 4.59 (d, J = 8.1 Hz, 1H), 2.09 (s, 3H), 1.44 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.96, 176.85, 161.51, 149.26, 148.40, 143.90, 142.72, 140.70, 138.53, 136.74, 130.92, 129.89, 129.28 (d, J = 3.5 Hz), 128.74, 128.14, 127.58, 127.34, 126.18, 125.77, 125.55, 125.19, 114.27, 84.60, 50.59, 49.22, 35.95, 31.72, 22.42
ESI-MS	[M+H]⁺ calculated for C₃₃H₃₁N₄O₂ is 515.2477, found 515.2477
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	97 % ee; t (minor) = 9.308 min, t (major) = 14.894 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-([1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3af
Specific rotation	[α]D²⁰ = 429.16 (c = 0.42, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.61 (dd, J = 10.0, 5.2 Hz, 1H), 7.79 (t, J = 7.8 Hz, 1H), 7.56 (d, J = 7.1 Hz, 2H), 7.47 (dt, J = 8.0, 4.2 Hz, 3H), 7.44 – 7.30 (m, 5H), 7.06 – 6.93 (m, 1H), 6.86 (d, J = 7.1 Hz, 2H), 6.72 (t, J = 7.6 Hz, 2H), 4.64 (d, J = 7.8 Hz, 1H), 4.45 (d, J = 7.6 Hz, 1H), 1.34 (s, 3H)
¹³C NMR (125 MHz, chloroform-d)	δ 176.06, 175.68, 175.23, 161.45, 149.21, 143.53, 140.89, 138.41, 137.57, 137.33, 130.60, 129.62, 128.88, 128.74, 128.48, 127.86, 127.77, 127.15, 125.14, 114.99, 84.57, 57.30, 50.33, 49.29, 22.34, 20.67
ESI-MS	[M+H]⁺ calculated for C₂₉H₂₃N₄O₂ is 458.1821, found 458.1818
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm; reported in SI)	99 % ee; t (major) = 24.769 min
Enantiomeric excess reported in Main	98 % ee
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(2-isopropylphenyl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ag
Specific rotation	[α]D²⁰ = 218.01 (c = 0.17, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.66 (dddd, J = 4.7, 3.8, 1.8, 0.8 Hz, 1H), 7.84 (td, J = 7.7, 1.9 Hz, 1H), 7.69 – 7.65 (m, 1H), 7.62 (t, J = 7.2 Hz, 1H), 7.54 (t, J = 8.2 Hz, 1H), 7.45 – 7.42 (m, 2H), 7.41 – 7.38 (m, 2H), 7.34 – 7.28 (m, 1H), 7.20 (ddd, J = 7.8, 7.0, 1.8 Hz, 1H), 7.11 (dd, J = 7.8, 1.4 Hz, 1H), 4.90 (dd, J = 72.8, 7.8 Hz, 1H), 4.58 (dd, J = 14.8, 7.8 Hz, 1H), 2.15 – 2.08 (m, 1H), 2.05 (s, 3H), 0.89 (d, J = 6.9 Hz, 3H), 0.83 (d, J = 6.9 Hz, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.10, 149.36, 146.38, 145.99, 143.83, 143.43, 138.49, 137.88, 130.04, 129.71, 129.35, 128.51, 128.12, 126.76, 126.49, 125.64, 125.53, 125.17, 115.18, 114.35, 84.73, 50.59, 49.32, 28.83, 28.13, 21.67
ESI-MS	[M+H]⁺ calculated for C₂₆H₂₅N₄O₂ is 425.1978, found 425.1969
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 70/30; 1.0 mL min⁻¹; λ = 254 nm)	92 % ee; t (minor) = 9.046 min, t (major) = 11.858 min
Diastereomeric ratio	3:1 dr

(S,3aR,8R,8aS)-2-(3-methoxy-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ah
Specific rotation	[α]D²⁰ = 144.44 (c = 0.42, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.64 (d, J = 4.9 Hz, 1H), 7.81 (td, J = 7.8, 2.0 Hz, 1H), 7.54 (dt, J = 16.1, 8.4 Hz, 3H), 7.46 – 7.30 (m, 9H), 7.03 (d, J = 7.7 Hz, 1H), 6.90 (d, J = 8.5 Hz, 1H), 4.68 (d, J = 8.3 Hz, 1H), 4.23 (d, J = 8.4 Hz, 1H), 3.54 (s, 3H), 2.00 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.90, 175.75, 161.60, 154.83, 149.22, 144.00, 142.97, 138.34 (d, J = 16.3 Hz), 137.13, 130.42, 129.49, 128.90, 128.32, 128.11, 127.78, 125.57, 125.39, 124.95, 122.29, 118.84, 114.24, 110.71, 84.78, 55.73, 50.55, 49.09, 22.34
ESI-MS	[M+H]⁺ calculated for C₃₀H₂₅N₄O₃ is 489.1927, found 489.1920
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	97 % ee; t (minor) = 27.615 min, t (major) = 17.732 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(3,4′-dimethoxy-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ai
Specific rotation	[α]D²⁰ = 261.467 (c = 0.32, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.64 (d, J = 4.8 Hz, 1H), 7.80 (td, J = 7.6, 1.9 Hz, 1H), 7.63 – 7.50 (m, 3H), 7.44 – 7.33 (m, 4H), 7.27 (s, 1H), 7.25 (s, 1H), 7.01 (d, J = 7.6 Hz, 1H), 6.93 (d, J = 8.6 Hz, 2H), 6.87 (d, J = 8.3 Hz, 1H), 4.72 (d, J = 8.3 Hz, 1H), 4.26 (d, J = 8.2 Hz, 1H), 3.85 (s, 3H), 3.52 (s, 3H), 2.00 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.93, 175.76, 161.59, 159.17, 154.81, 149.19, 144.00, 142.62, 138.41, 137.14, 130.47 (d, J = 33.8 Hz), 129.46, 129.21 (d, J = 4.4 Hz), 128.87, 125.46 (d, J = 22.8 Hz), 124.94, 122.35, 118.87, 114.19, 113.76, 110.37, 84.78, 55.68, 55.15, 50.55, 49.06, 22.33
ESI-MS	[M+H]⁺ calculated for C₃₁H₂₇N₄O₄ is 519.2032, found 519.1999
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 16.068 min, t (major) = 17.841 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(3-methoxy-4′-phenoxy-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3aj
Specific rotation	[α]D²⁰ = 261.47 (c = 0.21, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.65 (d, J = 4.8 Hz, 1H), 7.82 (t, J = 7.7 Hz, 1H), 7.56 (dt, J = 20.8, 7.5 Hz, 3H), 7.38 (td, J = 8.1, 2.9 Hz, 6H), 7.30 (d, J = 8.4 Hz, 2H), 7.21 – 7.08 (m, 3H), 7.02 (dd, J = 8.2, 3.9 Hz, 3H), 6.89 (d, J = 8.3 Hz, 1H), 4.73 (d, J = 8.2 Hz, 1H), 4.29 (d, J = 8.0 Hz, 1H), 3.53 (s, 3H), 2.01 (s, 3H)
¹³C NMR (126 MHz, chloroform-d)	δ 175.99, 175.83, 161.59, 157.32, 154.83, 149.24, 144.01, 142.38, 138.42, 137.15, 132.92, 130.43, 129.80, 129.53, 128.93, 125.58, 125.41, 124.98, 123.65, 122.36, 119.54, 118.08, 114.37, 110.62, 84.83, 55.72, 50.61, 49.18, 22.32
ESI-MS	[M+H]⁺ calculated for C₃₆H₂₉N₄O₄ is 581.2189, found 581.2183
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 35.529 min, t (major) = 21.799 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(3-methoxy-3′-methyl-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ak
Specific rotation	[α]D²⁰ = 273.76 (c = 0.40, CHCl₃)
¹H NMR (500 MHz, chloroform-d)	δ 8.76 – 8.59 (m, 1H), 7.81 (td, J = 7.8, 2.2 Hz, 1H), 7.63 – 7.57 (m, 1H), 7.56 – 7.49 (m, 2H), 7.43 – 7.33 (m, 4H), 7.28 (d, J = 7.8 Hz, 1H), 7.19 – 7.11 (m, 3H), 7.02 (d, J = 7.7 Hz, 1H), 6.89 (d, J = 8.3 Hz, 1H), 4.67 (d, J = 8.0 Hz, 1H), 4.26 (d, J = 8.2 Hz, 1H), 3.53 (s, 3H), 2.39 (s, 3H), 2.00 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.86, 175.79, 161.62, 154.80, 149.21, 144.00, 143.09, 138.41, 138.19, 137.94, 137.18, 130.35, 129.47, 128.91 (d, J = 6.6 Hz), 128.53, 128.08, 125.58, 125.37, 124.97 (d, J = 8.6 Hz), 122.35, 118.83, 114.36, 110.59, 84.76, 55.72, 50.58, 49.24, 22.32, 21.50
ESI-MS	[M+H]⁺ calculated for C₃₁H₂₇N₄O₃ is 503.2083, found 503.2083
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 34.218 min, t (major) = 28.315 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(3-methoxy-3′,5′-dimethyl-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3al
Specific rotation	[α]D²⁰ = 418.30 (c = 0.30, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.63 (d, J = 5.4 Hz, 1H), 7.80 (t, J = 8.1 Hz, 1H), 7.61 (d, J = 6.9 Hz, 1H), 7.52 (t, J = 7.9 Hz, 2H), 7.44 – 7.31 (m, 4H), 7.11 – 6.95 (m, 4H), 6.87 (d, J = 8.1 Hz, 1H), 4.65 (d, J = 8.2 Hz, 1H), 4.29 (d, J = 8.2 Hz, 1H), 3.50 (s, 3H), 2.35 (s, 6H), 2.01 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.83, 175.80, 161.62, 154.77, 149.20, 143.97, 143.22, 138.44, 138.16, 137.66, 137.24, 130.29, 129.46, 128.87, 125.88, 125.59, 125.36, 124.93, 122.41, 118.81, 114.59, 110.47, 84.74, 67.02, 55.72, 50.62, 49.46, 22.29, 21.39
ESI-MS	[M+H]⁺ calculated for C₃₃H₂₉N₄O₃ is 517.2240, found 517.2233
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 17.110 min, t (major) = 15.065 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-8-methyl-2-(3-methyl-[1,1′-biphenyl]-2-yl)-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3am
Specific rotation	[α]D²⁰ = 515.30 (c = 0.34, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.62 (dd, J = 5.0, 1.8 Hz, 1H), 7.80 (td, J = 7.8, 1.8 Hz, 1H), 7.60 (dd, J = 7.3, 1.6 Hz, 1H), 7.58 – 7.54 (m, 1H), 7.47 (d, J = 7.9 Hz, 1H), 7.46 – 7.31 (m, 7H), 7.34 – 7.26 (m, 3H), 7.23 (d, J = 8.0 Hz, 1H), 4.46 (d, J = 7.8 Hz, 1H), 4.23 (d, J = 7.9 Hz, 1H), 2.01 (s, 3H), 1.78 (s, 3H)
¹³C NMR (126 MHz, chloroform-d)	δ 175.71, 175.60, 161.52, 149.18, 143.38, 141.73, 138.85, 138.45, 137.40, 135.97, 129.99, 129.72, 129.45, 129.19, 128.82, 128.29, 128.15, 127.72, 125.36 (d, J = 12.4 Hz), 125.08, 114.54, 84.42, 50.25, 49.42, 21.85, 17.41
ESI-MS	[M+H]⁺ calculated for C₃₀H₂₅N₄O₂ is 473.1978, found 473.1971
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm; reported in SI)	99 % ee; t (minor) = 26.680 min, t (major) = 15.282 min
Enantiomeric excess reported in Main	>99 % ee
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(4′-ethyl-3-methyl-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3an
Specific rotation	[α]D²⁰ = 311.40 (c = 0.54, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.63 (dd, J = 5.0, 2.1 Hz, 1H), 7.86 – 7.74 (m, 1H), 7.61 (d, J = 6.7 Hz, 1H), 7.56 – 7.51 (m, 1H), 7.48 (dd, J = 8.3, 4.4 Hz, 1H), 7.43 – 7.30 (m, 5H), 7.22 (dt, J = 8.8, 4.4 Hz, 5H), 4.50 (d, J = 7.9 Hz, 1H), 4.26 (d, J = 7.9 Hz, 1H), 2.80 – 2.65 (m, 2H), 2.01 (s, 3H), 1.77 (s, 3H), 1.34 – 1.21 (m, 3H)
¹³C NMR (101 MHz, chloroform-d)	δ 175.77, 175.66, 161.61, 149.21, 143.58, 143.43, 141.79, 138.47, 137.49, 136.17, 135.92, 129.81, 129.73, 129.44, 129.20, 128.84, 128.52, 128.07, 127.84, 125.43, 125.35, 125.09, 114.52, 84.47, 50.31, 49.47, 28.49, 21.88, 17.45, 15.21
ESI-MS	[M+H]⁺ calculated for C₃₂H₂₉N₄O₂ is 501.2291, found 501.2285
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 18.833 min, t (major) = 22.915 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-8-methyl-2-(3-methyl-4′-(methylthio)-[1,1′-biphenyl]-2-yl)-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ao
Specific rotation	[α]D²⁰ = 329.60 (c = 0.39, CHCl₃)
¹H NMR (500 MHz, chloroform-d)	δ 8.63 (d, J = 5.0 Hz, 1H), 7.80 (td, J = 7.7, 1.8 Hz, 1H), 7.60 (d, J = 7.3 Hz, 1H), 7.55 (d, J = 7.3 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 7.43 – 7.30 (m, 5H), 7.28 (s, 1H) 7.24 – 7.19 (m, 4H), 4.52 (d, J = 7.8 Hz, 1H), 4.28 (d, J = 8.0 Hz, 1H), 2.52 (s, 3H), 2.01 (s, 3H), 1.76 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.70, 175.64, 161.45, 149.16, 143.33, 141.12, 138.45, 138.15, 137.37, 135.99, 135.41, 129.98, 129.72, 129.48, 129.20, 128.43 (d, J = 13.1 Hz), 125.95, 125.44, 125.26, 125.08, 114.59, 84.44, 50.26, 49.44, 21.80, 17.39, 15.33
ESI-MS	[M+H]⁺ calculated for C₃₁H₂₇N₄O₂S is 519.1855, found 519.1853
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 40.788 min, t (major) = 46.822 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(4′-(methoxymethyl)-3-methyl-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ap
Specific rotation	[α]D²⁰ = 299.47 (c = 0.37, CHCl₃)
¹H NMR (500 MHz, chloroform-d)	δ 8.64 – 8.59 (m, 1H), 7.80 (td, J = 7.8, 1.8 Hz, 1H), 7.60 (d, J = 7.1 Hz, 1H), 7.55 (d, J = 7.4 Hz, 1H), 7.48 (d, J = 7.9 Hz, 1H), 7.42 – 7.33 (m, 6H), 7.29 (d, J = 8.0 Hz, 2H), 7.22 (d, J = 8.3 Hz, 2H), 4.52 (s, 2H), 4.48 (d, J = 7.8 Hz, 1H), 4.24 (d, J = 7.8 Hz, 1H), 3.44 (s, 3H), 2.00 (s, 4H), 1.77 (s, 3H)
¹³C NMR (125 MHz, chloroform-d)	δ 175.69, 175.60, 161.47, 149.14, 143.35, 141.46, 138.46, 138.21, 137.61, 137.40, 135.97, 130.00, 129.71, 129.45, 129.20, 128.75, 128.42, 128.19, 127.59, 125.43, 125.28, 125.08, 114.57, 84.43, 74.34, 58.26, 50.24, 49.42, 21.80, 17.40
ESI-MS	[M+H]⁺ calculated for C₃₂H₂₉N₄O₃ is 517.2240, found 517.2234
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm; reported in SI)	97 % ee; t (minor) = 16.925 min, t (major) = 19.551 min
Enantiomeric excess reported in Main	98 % ee
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-2-(3′-chloro-3-methyl-[1,1′-biphenyl]-2-yl)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3aq
Specific rotation	[α]D²⁰ = 121.71 (c = 0.43, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.63 (dd, J = 4.8, 1.8 Hz, 1H), 7.81 (td, J = 7.7, 1.8 Hz, 1H), 7.69 – 7.63 (m, 3H), 7.58 (dd, J = 10.2, 7.7 Hz, 2H), 7.54 – 7.48 (m, 1H), 7.48 – 7.41 (m, 3H), 7.39 – 7.30 (m, 2H), 7.08 (dd, J = 7.8, 1.2 Hz, 1H), 6.92 (dd, J = 8.6, 1.3 Hz, 1H), 4.73 (d, J = 8.1 Hz, 1H), 4.28 (d, J = 8.2 Hz, 1H), 3.55 (s, 3H), 2.02 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 176.04, 175.87, 161.56, 154.87, 149.21, 144.00, 142.59, 140.50, 138.43, 137.20 (d, J = 11.1 Hz), 130.52, 129.51, 128.94, 128.75, 128.55, 127.37, 127.09, 125.59, 125.41, 124.99, 122.35, 118.83, 114.37, 110.78, 84.84, 55.76, 50.61, 49.19, 22.35
ESI-MS	[M+H]⁺ calculated for C₃₀H₂₄ClN₄O₂ is 507.1588, found 507.1587
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 22.298 min, t (major) = 33.588 min
Diastereomeric ratio	>20:1 dr

(S,3aR,8R,8aS)-8-methyl-8-((E)-pyridin-2-yldiazenyl)-2-(3′,4′,5′-trimethoxy-3-methyl-[1,1′-biphenyl]-2-yl)-8,8a-dihydroindeno[1,2-c]pyrrole-1,3(2H,3aH)-dione
Identifier	3ar
Specific rotation	[α]D²⁰ = 491.12 (c = 0.37, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.58 (dd, J = 4.8, 2.0 Hz, 1H), 7.83 – 7.73 (m, 1H), 7.60 (d, J = 6.5 Hz, 1H), 7.53 (dd, J = 7.0, 1.9 Hz, 1H), 7.51 – 7.43 (m, 1H), 7.39 – 7.33 (m, 3H), 7.30 (d, J = 0.9 Hz, 1H), 7.29 – 7.20 (m, 1H), 7.19 (d, J = 7.6 Hz, 1H), 6.53(s, 2H), 4.44 (d, J = 7.8 Hz, 1H), 4.28 (d, J = 7.8 Hz, 1H), 3.89 (s, 3H), 3.83 (s, 6H), 1.99 (s, 3H), 1.72 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.75, 175.52, 161.28, 152.69, 149.09, 143.23, 141.73, 138.39, 137.28 (d, J = 19.0 Hz), 136.01, 134.34, 129.76 (d, J = 23.6 Hz), 129.27 (d, J = 15.2 Hz), 128.70, 128.27, 125.37, 125.10 (d, J = 6.8 Hz), 115.17, 105.28, 84.37, 60.76, 55.98, 50.32, 49.87, 21.59, 17.22
ESI-MS	[M+H]⁺ calculated for C₃₃H₃₁N₄O₅ is 563.2294, found 563.2291
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 42.365 min, t (major) = 69.078 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(2-(tert-butyl)phenyl)-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8aa
Specific rotation	[α]D²⁰ = 297.12 (c = 0.26, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.23 (dd, J = 4.9, 2.9 Hz, 1H), 7.99 – 7.94 (m, 1H), 7.72 (td, J = 7.6, 1.2 Hz, 1H), 7.64 – 7.58 (m, 3H), 7.49 (dt, J = 7.7, 0.9 Hz, 1H), 7.47 – 7.40 (m, 1H), 7.33 (td, J = 7.5, 1.5 Hz, 1H), 6.94 – 6.85 (m, 2H), 6.80 – 6.76 (m, 1H), 3.98 (d, J = 19.3 Hz, 1H), 3.55 (s, 3H), 3.39 (d, J = 19.3 Hz, 1H), 1.39 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 174.69, 174.44, 165.61, 147.92, 142.03, 138.56, 133.31, 130.71, 130.25, 130.11, 128.79, 127.89, 121.22, 116.87, 107.45, 69.18, 39.59, 37.30, 35.59, 31.55
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₈N₃O₂ is 455.2083, found 455.2075
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 9.777 min, t (major) = 12.738 min
Diastereomeric ratio	>20:1 dr
Single-crystal XRD, formula and formula weight	C₂₇H₂₆N₄O₃; Mᵣ = 454.52 g mol⁻¹
Single-crystal XRD, crystal colour and size	Clear light colourless; 0.3 × 0.1 × 0.1 mm
Single-crystal XRD, crystal system and space group	Monoclinic, P2₁
Single-crystal XRD, unit cell	a = 8.6787(2) Å, b = 14.5563(4) Å, c = 9.5037(3) Å; α = 90°, β = 90.799(1)°, γ = 90°; V = 1200.48(6) Å³; Z = 4; Dcalc = 1.257 g cm⁻³
Single-crystal XRD, data collection	T = 273.15 K; λ = 0.71073 Å; μ(Mo-Kα) = 0.084 mm⁻¹; empirical absorption correction (Tₘᵢₙ = 0.6378, Tₘₐₓ = 0.7457); CCD Bruker APEX-II diffractometer; 2.143 < θ < 28.300
Single-crystal XRD, reflections	20763 measured; 5971 independent; 5348 with I > 2σ(I)
Single-crystal XRD, refinement	Structures were solved by direct methods and refined (SHELXL-97) by full matrix least squares based on F² to R₁ = 0.0419 [I > 2σ(I)], wR₂ = 0.1020; 311 parameters; H atoms riding; S = 1.039; residual electron density +0.251 / −0.251 e Å⁻³
Single-crystal XRD, CCDC deposition number	2575193

(R,S)-6-(tert-butyl)-1′-(2-(tert-butyl)phenyl)-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8ba
Specific rotation	[α]D²⁰ = 421.01 (c = 0.32, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.23 (dd, J = 4.9, 2.9 Hz, 1H), 7.87 (d, J = 8.1 Hz, 1H), 7.66 (dd, J = 8.1, 1.6 Hz, 1H), 7.61 – 7.57 (m, 2H), 7.50 (d, J = 1.5 Hz, 1H), 7.46 – 7.42 (m, 1H), 7.34 (td, J = 7.6, 1.5 Hz, 1H), 6.88 – 6.84 (m, 2H), 6.79 – 6.71 (m, 1H), 3.93 (d, J = 19.3 Hz, 1H), 3.55 (s, 3H), 3.40 (d, J = 19.4 Hz, 1H), 1.40 (s, 9H), 1.39 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 174.90, 174.67, 165.73, 159.83, 157.61, 148.21, 147.81, 142.21, 138.25, 130.79 (d, J = 4.1 Hz), 130.24, 128.64, 127.93, 127.63 (d, J = 10.1 Hz), 124.53, 117.81, 116.69, 107.24, 69.22, 39.39, 37.32, 35.67, 35.54, 31.44, 31.31
ESI-MS	[M+H]⁺ calculated for C₃₁H₃₆N₄O₃ is 511.2709, found 511.2701
Chiral HPLC (Daicel Chiralpak IF; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 9.844 min, t (major) = 11.560 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(2-(tert-butyl)phenyl)-6-methoxy-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8ca
Specific rotation	[α]D²⁰ = 311.09 (c = 0.38, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.23 (dd, J = 4.9, 2.9 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.59 (td, J = 7.8, 1.7 Hz, 2H), 7.44 (td, J = 7.7, 1.5 Hz, 1H), 7.33 (td, J = 7.5, 1.4 Hz, 1H), 7.11 (dd, J = 8.5, 2.2 Hz, 1H), 6.95 (d, J = 2.2 Hz, 1H), 6.90 – 6.82 (m, 2H), 6.75 (d, J = 8.4 Hz, 1H), 3.95 (d, J = 10.2 Hz, 1H), 3.91 (s, 3H), 3.53 (s, 3H), 3.35 (d, J = 19.3 Hz, 1H), 1.39 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 74.70, 165.51, 163.96, 148.25, 144.11, 138.26, 130.70, 130.31, 128.78, 126.45, 122.65, 116.70, 116.14, 107.25, 106.59, 68.89, 55.81, 39.51, 37.42, 35.58, 31.54
ESI-MS	[M+H]⁺ calculated for C₂₈H₃₀N₄O₄ is 485.2189, found 485.2179
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 15.312 min, t (major) = 25.740 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(2-(tert-butyl)phenyl)-2-(methyl(pyridin-2-yl)amino)-6-(methylthio)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8da
Specific rotation	[α]D²⁰ = 142.31 (c = 0.16, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.25 – 8.19 (m, 1H), 7.81 (dd, J = 8.2, 3.6 Hz, 1H), 7.65 – 7.54 (m, 2H), 7.49 – 7.38 (m, 2H), 7.39 – 7.28 (m, 1H), 7.28 (dd, J = 4.3, 1.7 Hz, 1H), 6.90 – 6.82 (m, 2H), 6.82 – 6.69 (m, 1H), 3.95 (d, J = 19.2 Hz, 1H), 3.53 (s, 3H), 3.36 (d, J = 19.2 Hz, 1H), 2.55 (s, 3H), 1.39 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 174.57, 174.39, 165.38, 159.65, 148.19, 147.71, 146.56, 142.82, 138.26, 130.61 (d, J = 12.3 Hz), 130.25, 128.76, 127.89, 126.99, 126.59, 124.85, 117.54, 116.79, 107.23, 68.89, 39.45, 37.20, 35.56, 31.51, 15.14
ESI-MS	[M+H]⁺ calculated for C₂₈H₃₀N₄O₃S is 501.1960, found 501.1958
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	94 % ee; t (minor) = 31.400 min, t (major) = 39.594 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(2-(tert-butyl)phenyl)-6-chloro-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8ea
Specific rotation	[α]D²⁰ = 427.51 (c = 0.25, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.20 (dd, J = 4.9, 2.8 Hz, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.75 (dd, J = 8.1, 1.6 Hz, 1H), 7.67 – 7.59 (m, 3H), 7.47 – 7.41 (m, 1H), 7.33 (td, J = 7.5, 1.5 Hz, 1H), 6.90 – 6.83 (m, 2H), 6.81 – 6.77 (m, 1H), 4.02 (d, J = 19.3 Hz, 1H), 3.52 (s, 3H), 3.36 (d, J = 19.3 Hz, 1H), 1.40 (s, 9H)
¹³C NMR (101 MHz, chloroform-d)	δ 174.16, 174.06, 164.78, 159.35, 148.23, 147.81, 143.53, 138.34, 133.46, 130.60, 130.35 (d, J = 10.0 Hz), 128.86, 127.84, 126.23, 124.89, 117.04, 107.29, 68.80, 39.48, 37.00, 35.60, 31.47
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₇ClN₄O₃ is 489.1693, found 489.1693
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 82/18; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 36.921 min, t (major) = 49.184 min
Diastereomeric ratio	>20:1 dr

(R,S)-6-bromo-1′-(2-(tert-butyl)phenyl)-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8fa
Specific rotation	[α]D²⁰ = 146.91 (c = 0.19, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.22 (dd, J = 4.9, 2.8 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.75 (dd, J = 8.1, 1.5 Hz, 1H), 7.66 – 7.59 (m, 3H), 7.44 (td, J = 7.7, 1.5 Hz, 1H), 7.33 (td, J = 7.5, 1.5 Hz, 1H), 6.94 – 6.84 (m, 1H), 6.85 (dd, J = 7.8, 1.5 Hz, 1H), 6.80 – 6.76 (m, 1H), 4.00 (d, J = 19.3 Hz, 1H), 3.52 (s, 3H), 3.36 (d, J = 19.3 Hz, 1H), 1.39 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 174.16, 174.05, 164.86, 159.37, 148.19, 147.85, 143.57, 138.45, 133.48, 131.78, 130.63, 130.43, 130.31, 130.09, 129.36, 128.88, 128.41, 127.83 (d, J = 6.0 Hz), 126.26, 124.91, 117.07, 107.38, 68.86, 39.55, 37.01, 35.62, 31.47
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₇BrN₄O₃ is 533.1188, found 533.1185
Chiral HPLC (Daicel Chiralpak IF; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	>99 % ee; t (major) = 41.290 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(4-bromo-2-(tert-butyl)phenyl)-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8ac
Specific rotation	[α]D²⁰ = 299.90 (c = 0.56, CHCl₃)
¹H NMR (500 MHz, chloroform-d)	δ 8.21 (dd, J = 5.0, 2.8 Hz, 1H), 7.94 (dt, J = 7.5, 1.0 Hz, 1H), 7.78 – 7.67 (m, 2H), 7.67 – 7.56 (m, 2H), 7.51 – 7.42 (m, 2H), 6.87 (dd, J = 7.8, 5.3 Hz, 1H), 6.78 (d, J = 8.4 Hz, 1H), 6.73 (d, J = 8.3 Hz, 1H), 4.01 (d, J = 19.4 Hz, 1H), 3.52 (s, 3H), 3.38 (d, J = 19.3 Hz, 1H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 174.57, 174.17, 165.51, 159.61, 150.18, 148.20, 141.76, 138.32, 133.29, 132.26, 132.13, 131.02, 130.41, 130.16, 129.76, 124.90, 124.58, 121.11, 116.96, 107.31, 69.16, 39.48, 37.21, 35.71, 31.28
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₇BrN₄O₃ is 533.1188, found 533.1179
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 9.265 min, t (major) = 12.765 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(2-(tert-butyl)-4-iodophenyl)-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8ad
Specific rotation	[α]D²⁰ = 179.67 (c = 0.30, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.21 (dd, J = 4.9, 2.8 Hz, 1H), 7.95 – 7.93 (m, 1H), 7.90 (d, J = 1.9 Hz, 1H), 7.71 (td, J = 7.6, 1.2 Hz, 1H), 7.66 (dd, J = 8.2, 2.0 Hz, 1H), 7.64 – 7.58 (m, 2H), 7.48 – 7.45 (m, 1H), 6.92 – 6.83 (m, 1H), 6.79 – 6.76 (m, 1H), 6.57 (d, J = 8.2 Hz, 1H), 4.00 (d, J = 19.3 Hz, 1H), 3.52 (s, 3H), 3.37 (d, J = 19.3 Hz, 1H), 1.36 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 174.54, 174.15, 165.52, 159.61, 150.20, 148.21, 141.77, 138.32, 138.16, 137.07, 133.29, 132.34, 130.57, 130.41, 130.16, 124.91, 121.12, 116.96, 107.31, 96.85, 69.17, 39.48, 37.22, 35.58, 31.30
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₇IN₄O₃ is 581.1050, found 581.1055
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	95 % ee; t (minor) = 22.816 min, t (major) = 19.116 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(3-methoxy-[1,1′-biphenyl]-2-yl)-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8ah
Specific rotation	[α]D²⁰ = 184.70 (c = 0.34, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.26 (d, J = 8.4 Hz, 1H), 7.67 (d, J = 8.6 Hz, 1H), 7.58 (s, 1H), 7.51 (t, J = 7.6 Hz, 1H), 7.35 – 7.29 (m, 3H), 7.20 – 7.15 (m, 2H), 7.12 – 7.05 (m, 4H), 6.92 (s, 1H), 6.75 (d, J = 8.1 Hz, 2H), 6.32 (d, J = 8.3 Hz, 1H), 3.91 (s, 3H), 3.72 (d, J = 18.9 Hz, 1H), 3.56 (s, 3H), 3.20 (s, 1H)
¹³C NMR (100 MHz, chloroform-d)	δ 174.56, 174.45, 160.40, 150.10, 144.01, 141.69, 137.97, 137.47, 136.65, 135.04, 130.87, 129.10, 128.47, 128.34, 127.92, 127.80, 126.94, 126.80, 125.68, 124.20, 123.97, 122.48, 122.20, 120.36, 114.59, 112.23, 22.96, 21.41
ESI-MS	[M+H]⁺ calculated for C₃₀H₂₆N₄O₄ is 505.1876, found 505.1870
Chiral HPLC (Daicel Chiralpak IF; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 32.589 min, t (major) = 15.297 min
Diastereomeric ratio	>20:1 dr

(R,S)-1′-(3′-chloro-3-methyl-[1,1′-biphenyl]-2-yl)-2-(methyl(pyridin-2-yl)amino)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8am
Specific rotation	[α]D²⁰ = 290.29 (c = 0.46, CHCl₃)
¹H NMR (500 MHz, chloroform-d)	δ 8.21 (dd, J = 5.1, 1.8 Hz, 1H), 7.80 (d, J = 7.6 Hz, 1H), 7.74 – 7.65 (m, 3H), 7.57 – 7.51 (m, 3H), 7.40 – 7.35 (m, 2H), 7.10 – 7.02 (m, 2H), 6.85 – 6.77 (m, 1H), 6.62 (d, J = 8.5 Hz, 1H), 6.24 (d, J = 7.6 Hz, 1H), 3.88 (s, 3H), 3.69 (d, J = 18.9 Hz, 1H), 3.51 (s, 3H), 3.03 (d, J = 18.9 Hz, 1H)
¹³C NMR (100 MHz, chloroform-d)	δ 173.67, 173.55, 165.78, 159.35, 154.73, 148.18, 142.80, 142.27, 140.74, 140.26, 138.08, 137.30, 133.07, 130.98, 129.64, 129.06, 128.91, 128.77, 127.75, 127.02, 126.91, 124.37, 122.35, 120.65, 118.56, 116.09, 110.97, 106.70, 69.02, 56.14, 38.51, 36.38
ESI-MS	[M+H]⁺ calculated for C₃₀H₂₅ClN₄O₃ is 523.1537, found 523.1531
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 80/20; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 30.066 min, t (major) = 41.756 min
Diastereomeric ratio	>20:1 dr

(R,S)-2-(methyl(pyridin-2-yl)amino)-1′-(3-methyl-[1,1′-biphenyl]-2-yl)spiro[isoindoline-1,3′-pyrrolidine]-2′,3,5′-trione
Identifier	8aq
Specific rotation	[α]D²⁰ = 518.01 (c = 0.57, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.19 (dd, J = 4.9, 1.9 Hz, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.61 – 7.49 (m, 2H), 7.47 – 7.39 (m, 4H), 7.33 (td, J = 7.6, 1.3 Hz, 1H), 7.21 (dd, J = 7.3, 1.8 Hz, 1H), 6.85 (dd, J = 7.3, 4.9 Hz, 1H), 6.69 (d, J = 8.4 Hz, 1H), 5.89 (d, J = 7.7 Hz, 1H), 3.82 (d, J = 19.0 Hz, 1H), 3.50 (s, 3H), 3.02 (d, J = 19.0 Hz, 1H), 2.23 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 173.67, 173.34, 165.78, 159.69, 148.23, 142.15, 141.77, 139.17, 138.23, 135.84, 133.16, 130.41, 129.79, 129.64, 129.49, 128.60 (d, J = 9.6 Hz), 127.64, 124.25, 120.88, 116.74, 107.19, 69.34, 39.55, 36.70, 17.50
ESI-MS	[M+H]⁺ calculated for C₃₀H₂₆N₄O₃ is 489.1927, found 489.1922
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 13.164 min, t (major) = 10.807 min
Diastereomeric ratio	>20:1 dr

methyl (R)-1-(2-(methyl(pyridin-2-yl)amino)-2′,3,5′-trioxospiro[isoindoline-1,3′-pyrrolidin]-1′-yl)-1H-indole-2-carboxylate
Identifier	8as
Specific rotation	[α]D²⁰ = 396.00 (c = 0.33, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.26 (dd, J = 5.4, 1.5 Hz, 1H), 8.04 (d, J = 7.8 Hz, 1H), 7.92 (d, J = 7.4 Hz, 1H), 7.83 – 7.71 (m, 2H), 7.64 (dt, J = 15.5, 7.5 Hz, 2H), 7.50 – 7.38 (m, 2H), 7.13 (d, J = 8.5 Hz, 1H), 6.92 (dd, J = 7.3, 4.9 Hz, 1H), 6.87 (d, J = 8.4 Hz, 1H), 4.23 (d, J = 19.4 Hz, 1H), 3.94 (s, 4H), 3.57 (s, 3H), 3.53 (d, J = 19.1 Hz, 1H)
¹³C NMR (100 MHz, chloroform-d)	δ 171.26, 170.46, 165.75, 160.72, 159.66, 148.30, 142.15, 138.45, 137.83, 133.77, 130.13, 129.94, 127.35, 125.12, 124.66, 124.36, 123.49, 122.88 (d, J = 3.0 Hz), 117.12, 112.12, 108.41, 107.42, 67.48, 52.09, 39.76, 36.00
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₂N₅O₅ is 496.1621, found 496.1612
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	99 % ee; t (minor) = 15.592 min, t (major) = 19.836 min
Diastereomeric ratio	>20:1 dr

methyl (R)-5-methyl-1-(2-(methyl(pyridin-2-yl)amino)-2′,3,5′-trioxospiro[isoindoline-1,3′-pyrrolidin]-1′-yl)-1H-indole-2-carboxylate
Identifier	8at
Specific rotation	[α]D²⁰ = 505.26 (c = 0.49, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.25 (dd, J = 4.8, 2.2 Hz, 1H), 8.03 (d, J = 7.7 Hz, 1H), 7.91 (d, J = 7.7 Hz, 1H), 7.76 (td, J = 7.6, 1.3 Hz, 1H), 7.70 – 7.56 (m, 2H), 7.36 (d, J = 0.9 Hz, 1H), 7.15 – 7.08 (m, 2H), 7.03 (d, J = 8.9 Hz, 1H), 6.91 (dd, J = 7.3, 4.9 Hz, 1H), 6.87 (d, J = 8.5 Hz, 1H), 4.21 (d, J = 19.3 Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.56 (s, 3H), 3.52 (d, J = 19.3 Hz, 1H)
¹³C NMR (100 MHz, chloroform-d)	δ 171.29, 170.47, 165.71, 160.63, 159.63, 156.17, 148.27, 142.13, 138.42, 133.74, 133.06, 130.09, 129.91, 125.46, 124.31, 122.83, 118.50, 117.09, 111.66, 109.34, 107.40, 103.85, 67.43, 55.76, 52.00, 39.70, 35.96, 29.64
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₄N₅O₅ is 510.1777, found 510.1770
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm; reported in SI)	99 % ee; t (minor) = 23.959 min, t (major) = 16.323 min
Enantiomeric excess reported in Main	97 % ee
Diastereomeric ratio	>20:1 dr

methyl (R)-5-methoxy-1-(2-(methyl(pyridin-2-yl)amino)-2′,3,5′-trioxospiro[isoindoline-1,3′-pyrrolidin]-1′-yl)-1H-indole-2-carboxylate
Identifier	8au
Specific rotation	[α]D²⁰ = 301.87 (c = 0.31, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.26 (dd, J = 4.9, 2.8 Hz, 1H), 8.03 (d, J = 7.8 Hz, 1H), 7.91 (d, J = 7.5 Hz, 1H), 7.76 (td, J = 7.7, 1.3 Hz, 1H), 7.71 – 7.57 (m, 2H), 7.54 – 7.51 (m, 1H), 7.37 (s, 1H), 7.30 – 7.26 (m, 1H), 7.03 (d, J = 8.5 Hz, 1H), 6.91 (dd, J = 7.3, 5.7 Hz, 1H), 6.86 (d, J = 8.6 Hz, 1H), 4.21 (d, J = 19.3 Hz, 1H), 3.92 (s, 3H), 3.56 (s, 3H), 3.52 (d, J = 19.2 Hz, 1H), 2.46 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 171.25, 170.46, 165.74, 160.75, 159.66, 148.30, 142.16, 138.40, 136.32, 133.74, 132.45, 130.09, 129.91, 129.16, 125.02 (d, J = 24.2 Hz), 124.32, 122.84, 117.07, 111.73, 108.09, 107.37, 67.45, 51.99, 39.69, 35.95, 21.31
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₄N₅O₆ is 526.1727, found 526.1717
Chiral HPLC (Daicel Chiralpak IA; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	97 % ee; t (minor) = 26.086 min, t (major) = 17.428 min
Diastereomeric ratio	>20:1 dr

methyl (R)-5-bromo-1-(2-(methyl(pyridin-2-yl)amino)-2′,3,5′-trioxospiro[isoindoline-1,3′-pyrrolidin]-1′-yl)-1H-indole-2-carboxylate
Identifier	8av
Specific rotation	[α]D²⁰ = 307.01 (c = 0.38, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.29 – 8.21 (m, 1H), 8.04 – 8.00 (m, 1H), 7.92 – 7.89 (m, 2H), 7.82 – 7.72 (m, 1H), 7.71 – 7.57 (m, 2H), 7.59 – 7.49 (m, 1H), 7.38 (s, 1H), 7.02 (dd, J = 8.7, 4.4 Hz, 1H), 6.96 – 6.84 (m, 2H), 4.26 (d, J = 19.3 Hz, 1H), 3.94 (s, 3H), 3.58 – 3.47 (m, 4H)
¹³C NMR (100 MHz, chloroform-d)	δ 171.11, 170.18, 165.65, 160.33, 159.63, 148.31, 141.97, 138.45, 136.40, 133.77, 130.23 (d, J = 10.2 Hz), 129.91, 126.13, 125.84, 124.37, 122.79, 117.22, 115.96, 111.05, 109.97, 107.42, 67.46, 52.25, 39.73, 36.04, 29.65
ESI-MS	[M+H]⁺ calculated for C₂₇H₂₁BrN₅O₅ is 574.0726, found 574.0720
Chiral HPLC (Daicel Chiralpak IC; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 48.384 min, t (major) = 34.568 min
Diastereomeric ratio	>20:1 dr

ethyl (R)-1-(2-(methyl(pyridin-2-yl)amino)-2′,3,5′-trioxospiro[isoindoline-1,3′-pyrrolidin]-1′-yl)-1H-indole-2-carboxylate
Identifier	8aw
Specific rotation	[α]D²⁰ = 275.11 (c = 0.29, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.30 – 8.23 (m, 1H), 8.05 (d, J = 7.7 Hz, 1H), 7.92 (dt, J = 7.5, 0.9 Hz, 1H), 7.81 – 7.72 (m, 2H), 7.69 – 7.59 (m, 2H), 7.50 – 7.38 (m, 2H), 7.32 – 7.25 (m, 1H), 7.15 (d, J = 8.4 Hz, 1H), 6.93 – 6.85 (m, 2H), 4.40 (q, J = 6.8 Hz, 2H), 4.24 (d, J = 19.2 Hz, 1H), 3.59 (s, 3H), 3.54 (d, J = 19.2 Hz, 1H), 1.40 (t, J = 7.1 Hz, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 171.27, 170.46, 165.73, 160.30, 159.62, 148.23, 142.17, 138.45, 137.81, 133.73, 130.09, 129.91, 127.23, 125.42, 124.66, 124.31, 123.42, 122.85 (d, J = 4.7 Hz), 117.08, 111.91, 108.38, 107.41, 67.45, 61.17, 39.74, 35.97, 29.65, 14.18
ESI-MS	[M+H]⁺ calculated for C₂₈H₂₄N₅O₅ is 510.1777, found 510.1701
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	94 % ee; t (minor) = 11.800 min, t (major) = 13.719 min
Diastereomeric ratio	>20:1 dr

mer-(S,R)-[∆Co]
¹H NMR (400 MHz, chloroform-d)	δ 10.51 (s, 1H), 8.50 (d, J = 5.3 Hz, 1H), 7.84 – 7.74 (m, 2H), 7.39 (d, J = 7.5 Hz, 2H), 7.34 (d, J = 7.1 Hz, 2H), 7.11 (d, J = 7.4 Hz, 1H), 7.05 – 6.99 (m, 2H), 6.87 (dt, J = 12.8, 6.9 Hz, 1H), 6.76 (t, J = 7.9 Hz, 2H), 6.36 (t, J = 7.7 Hz, 1H), 6.19 (d, J = 6.8 Hz, 1H), 4.44 – 4.37 (m, 2H), 3.68 (t, J = 9.1 Hz, 1H), 3.54 – 3.52 (m, 1H), 3.50 – 3.44 (m, 1H), 2.87 (s, 6H), 1.26 (s, 9H), 0.29 (d, J = 6.3 Hz, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 177.17, 175.82, 168.57, 165.74, 159.51, 154.12, 151.30, 148.4, 145.0, 142.6, 139.0, 134.0, 131.3, 130.1, 128.62, 128.56, 12.74, 123.6, 117.4, 113.3, 113.1, 109.6, 106.9, 73.9, 67.9, 67.0, 65.9, 39.1, 28.1, 27.4, 26.49, 14.1, 10.6
ESI-MS	[M+H]⁺ calculated for C₃₅H₃₉BrCoN₆O₄ is 745.1548, found 745.1535

H/D exchange in absence of N-arylmaleimides
Identifier	1a-CD₄
¹H NMR analysis after H/D exchange (DCE, air, 60 °C, 6 h)	12 % H/D exchange occurs at the each ortho-position of the purified compound 1a-CD₄

H/D exchange in presence of N-arylmaleimides
¹H NMR analysis of 3aa-CD₄ after H/D exchange (DCE, air, room temperature, 4 h)	20 % H incorporation at the ortho position
¹H NMR analysis of 1a-D₅ after H/D exchange (DCE, air, room temperature, 4 h)	4 % H incorporation at the both ortho position

Parallel KIE experiment
¹H NMR-determined yield of 3aa over reaction time (DCE, 60 °C; 1,2-dibromoethane internal standard)	1 h: 14 %; 2 h: 21 %; 3 h: 35 %; 4 h: 42 %
¹H NMR-determined yield of 3aa-D₄ over reaction time (DCE, 60 °C; 1,2-dibromoethane internal standard)	1 h: 6 %; 2 h: 14 %; 3 h: 22 %; 4 h: 31 %
Kinetic isotope effect (DCE, 0.2 M, 60 °C, 2–8 h, air)	1.18

Intermolecular competitive experiment
Crude ¹H NMR analysis (DCE, air, 60 °C, 6 h)	3ba:3la = 6.6: 1.0

Compound 4
Identifier	4
Specific rotation	[α]D²⁰ = 680.7 (c = 0.32, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 7.86 (dd, J = 5.2, 1.8 Hz, 1H), 7.58 – 7.44 (m, 2H), 7.45 – 7.34 (m, 2H), 7.35 – 7.33 (m, 4H), 7.31 – 7.28 (m, 3H), 7.10 – 6.97 (m, 2H), 6.88 (dd, J = 8.3, 1.2 Hz, 1H), 6.66 – 6.57 (m, 1H), 4.68 (d, J = 8.2 Hz, 1H), 4.16 (d, J = 8.3 Hz, 1H), 3.53 (d, J = 6.3 Hz, 1H), 3.50 (s, 3H), 1.68 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.90, 175.75, 161.61, 154.85, 149.20, 144.01, 142.99, 138.45, 138.27, 137.15, 130.43, 129.49, 128.91, 128.32, 128.12, 127.79, 125.58, 125.39, 124.96, 122.30, 118.88, 114.25, 110.74, 84.79, 55.74, 50.56, 49.16, 22.33
ESI-MS	[M+H]⁺ calculated for C₃₀H₂₇N₄O₃ is 491.2083, found 491.2077
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 90/10; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 18.753 min, t (major) = 24.223 min
Diastereomeric ratio	>20:1 dr

Compound 5
Identifier	5
Specific rotation	[α]D²⁰ = 181.25 (c = 0.27, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 7.55 (d, J = 6.3 Hz, 1H), 7.41 (t, J = 8.2 Hz, 1H), 7.41 – 7.32 (m, 2H), 7.19 – 7.14 (m, 1H), 7.01 (d, J = 8.4 Hz, 1H), 6.91 (dd, J = 6.4, 5.2 Hz, 2H), 6.86 – 6.81 (m, 2H), 6.67 (td, J = 8.0, 1.7 Hz, 2H), 4.51 (d, J = 7.8 Hz, 1H), 3.86 (s, 3H), 3.47 (d, J = 7.9 Hz, 1H), 2.65 (s, 2H), 1.26 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.93, 174.36, 155.23, 148.18, 142.69, 137.34, 136.02, 130.52, 129.04 (d, J = 7.1 Hz), 127.85, 127.60, 127.20, 125.19, 122.91, 122.11, 118.31, 110.80, 63.97, 57.44, 56.05, 50.12, 29.65
ESI-MS	[M+H]⁺ calculated for C₂₅H₂₃N₂O₃ is 399.1709, found 399.1717
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 95/05; 1.0 mL min⁻¹; λ = 254 nm)	91 % ee; t (minor) = 14.719 min, t (major) = 15.948 min
Diastereomeric ratio	>20:1 dr

Compound 6
Identifier	6
Specific rotation	[α]D²⁰ = 305.19 (c = 0.29, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 7.99 – 7.94 (m, 1H), 7.56 (dd, J = 7.3, 1.7 Hz, 1H), 7.55 – 7.44 (m, 1H), 7.45 – 7.35 (m, 2H), 7.39 – 7.31 (m, 2H), 7.33 – 7.30 (m, 5H), 7.04 – 6.99 (m, 2H), 6.89 (d, J = 8.2 Hz, 1H), 6.68 – 6.64 (m, 1H), 5.65 (s, 1H), 4.13 (d, J = 8.2 Hz, 1H), 3.52 (s, 3H), 3.47 (d, J = 8.2 Hz, 1H), 1.67 (s, 3H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.92 (d, J = 5.3 Hz), 175.77 (d, J = 5.7 Hz), 161.64, 159.92, 154.83, 149.26, 145.06, 144.03, 142.99, 138.73, 138.36 (d, J = 15.1 Hz), 137.51, 137.15, 130.44, 129.46 (d, J = 11.5 Hz), 128.96 (d, J = 7.8 Hz), 128.33 (d, J = 4.8 Hz), 128.12 (d, J = 3.7 Hz), 127.78 (d, J = 6.5 Hz), 125.78, 125.61, 125.41, 124.98, 122.89, 122.34, 118.84 (d, J = 5.6 Hz), 114.59, 114.27, 110.71 (d, J = 5.6 Hz), 108.07, 84.81, 71.14, 55.70 (d, J = 13.3 Hz), 52.56, 50.56, 49.12, 22.50, 14.10
ESI-MS	[M+H]⁺ calculated for C₃₃H₂₇N₄O₃ is 491.2083, found 491.2080
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	98 % ee; t (minor) = 14.327 min, t (major) = 16.414 min
Diastereomeric ratio	>20:1 dr

Compound 9
Identifier	9
Specific rotation	[α]D²⁰ = 305.19 (c = 0.29, CHCl₃)
¹H NMR (400 MHz, chloroform-d)	δ 8.75 (s, 1H), 7.87 (d, J = 7.5 Hz, 1H), 7.66 (t, J = 7.6 Hz, 1H), 7.60 – 7.52 (m, 2H), 7.48 (d, J = 7.8 Hz, 1H), 7.36 (t, J = 7.4 Hz, 1H), 7.22 – 7.16 (m, 2H), 3.43 (s, 2H), 1.37 (s, 9H)
¹³C NMR (100 MHz, chloroform-d)	δ 175.19, 174.72, 170.70, 147.64, 145.02, 133.04, 131.93, 131.00, 130.05 (d, J = 2.5 Hz), 128.35, 127.83, 124.89, 121.21, 64.72, 60.41, 40.51, 35.48, 31.53, 29.66, 14.16
ESI-MS	[M+H]⁺ calculated for C₂₁H₂₁N₂O₃ is 349.1552, found 349.1544
Chiral HPLC (Daicel Chiralpak IB; hexane/IPA = 85/15; 1.0 mL min⁻¹; λ = 254 nm)	97 % ee; t (minor) = 23.367 min, t (major) = 19.337 min
Diastereomeric ratio	>20:1 dr