Compound 3p

(3S,3''S,2'R,5'S)-1-Acetyl-1''-benzyl-dispiro[6-chloro-oxindole-3,1'-[5'-hydroxy-2'-methoxycarbonyl-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 GYDJJDODUAATNY-QYSAAILDSA-N

Compound data: CIF

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

Compound 3p was synthesized by the general method outlined for compound 3a, replacing 2a with 2f. 1H-NMR (500 MHz, CDCl3) δ 8.13 (d, J = 7.5 Hz, 1H), 8.10 (J = 2.0 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.35-7.12 (m, 11H), 7.05-7.03 (m, 2H), 6.94 (s, 1H), 6.78 (d, J = 7.5 Hz, 1H), 5.30 (d, J = 15.5 Hz, 1H), 4.83 (d, J = 16.0 Hz, 1H), 4.49 (s, 1H), 4.25 (d, J = 14.0 Hz, 1H), 2.94 (s, 3H), 2.65 (d, J = 14.5 Hz, 1H), 2.41 (s, 3H). 13C-NMR (125 MHz, CDCl3) δ 183.44, 177.92, 170.83, 168.65, 141.96, 141.23, 137.31, 134.87, 134.00, 132.08, 129.71, 129.38, 129.17, 128.75, 128.55, 128.04, 127.40, 125.99, 125.87, 15.65, 124.95, 117.34, 116.26, 111.29, 85.77, 67.91, 62.05, 54.70, 52.21, 46.05, 44.91, 26.78. HPLC: Chiralpak AD-H (hexane/i-PrOH = 90/10, flow rate 2 mL/min, λ = 254 nm), tR (minor) = 11.4 min, tR (major) = 14.3 min; 94:6 er. [α]D25 = +93.2 (c = 0.5, CH2Cl2). IR (CH2Cl2) ν 3392.8, 2942.5, 1750.2, 1715.1, 1682,9, 1610.3,1470.6, 1390.0, 1287.6, 1168.1, 749.6.cm-1. HRMS (ESI) calcd for [M+H] C36H30ClN2O6, m/z: 621.1787, observed: 621.1793.

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