Compound 3e

(3S,3''S,2'R,5'S)-1-Acetyl-1''-benzyl-dispiro[oxindole-3,1'-[2'-(4-chloro-benzoyl)-5'-hydroxy-5'-phenyl]-cyclopentane-3',3''-oxindole]

From: Construction of bispirooxindoles containing three quaternary stereocentres in a cascade using a single multifunctional organocatalyst

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InChIKey KQJBNWLIQOTVBY-GJNWKUNXSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Compound 3e was synthesized by the general method outlined for compound 3b, replacing 2b with 2c. 1H-NMR (500 MHz, CDCl3) δ 8.06 (d, J = 8.0 Hz, 1H), 7.99-7.97 (m,1H), 7.94 (d, J = 7.5 Hz, 1H), 7.42-7.32 (m, 6H), 7.29-7.25 (m, 1H), 7.19-7.15 (m, 1H), 7.12-7.09 (m, 1H), 7.05-6.99 (m, 6H), 6.92 (s, 1H), 6.80-6.78 (m, 2H), 6.52-6.50 (m, 2H), 5.33 (s, 1H), 5.07 (d, J = 15.0 Hz, 1H), 4.59 (d, J = 15.0 Hz, 1H), 4.30 (d, J = 14.0 Hz, 1H), 2.58 (d, J = 14.0 Hz, 1H), 2.46 (s, 3H). 13C-NMR (125 MHz, CDCl3) δ 195.39, 183.95, 178.43, 170.98, 142.12, 139.39, 137.48, 130.41, 135.21, 135.11, 130.41, 129.58, 129.20, 128.74, 128.63, 128.60, 127.98, 126.73, 126.15, 126.02, 125.66, 124.90, 116.32, 109.23, 85.28, 67.76, 66.08, 54.56, 47.13, 45.27, 26.85. HPLC: Chiralpak AD-H (hexane/i-PrOH = 90/10, flow rate: 2 mL/min, λ = 254 nm), tR (minor) = 5.2 min, tR (major) = 11.4 min; 97:3 er. [α]D25 = +168.0 (c = 0.5, CH2Cl2). IR (CH2Cl2) ν 3322.7, 2919.8, 2235.1, 1747.8, 1680.0, 1610.7, 1481.1, 1296.1, 750.5 cm-1. HRMS (ESI) calcd for [M+H] C41H32ClN2O5, m/z: 667.1994, observed: 667.1976.

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