Compound 3b

(3S,3''S,2'R,5'S)-1-Acetyl-1''-benzyl-dispiro[oxindole-3,1'-[2'-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 DTHFLBIXUMHPHD-GJNWKUNXSA-N

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

The multifunctional catalyst VIII (0.0075 mmol, 0.15 equiv) was added to a solution of 3-substituted oxindole 1a (0.05 mmol, 1.0 equiv) and methyleneindolinone 2b (0.075 mmol, 1.5 equiv) in DCM (0.2-0.4 mL) at room temperature (23 °C). After 24 hours, the product 3b was afforded by silica gel flash column chromatography using gradient elution (EtOAc/Hexane = 1:10 to 1:8). 1H-NMR (500 MHz, CDCl3) δ 8.07 (d, J = 8.0 Hz, 1H), 8.01 (d, J = 7.5 Hz, 1H), 7.96 (d, J = 7.5 Hz, 1H), 7.37-7.23 (m, 8H), 7.19-7.09 (m, 5H), 7.04-6.95 (m, 7H), 6.36 (d, J = 8.0 Hz, 1H), 5.32 (s, 1H), 5.22 (d, J = 15.5 Hz, 1H), 4.37 (d, J = 15.5 Hz, 1H), 4.32 (d, J = 14.0 Hz, 1H), 2.59 (d, J = 14.0 Hz, 1H), 2.48 (s, 3H). 13C-NMR (125 MHz, CDCl3) δ 196.55, 184.10, 178.53, 171.03, 142.13, 141.37, 137.59, 135.20, 132.98, 130.50, 129.49, 129.44, 128.99, 128.60, 128.56, 128.32, 128.22, 127.97, 127.48, 126.68, 126.32, 126.05, 125.68, 124.88, 124.62, 116.31, 109.18, 85.33, 67.71, 66.32, 54.62, 46.97, 45.06, 26.87. HPLC: Chiralpak AD-H (hexane/i-PrOH = 90/10, flow rate 2 mL/min, λ = 254 nm), tR (minor) = 9.6 min, tR (major) = 18.8 min; 97:3 er. [α]D25 = +96.9 (c = 0.9, CH2Cl2). IR (CH2Cl2) ν 3329.6, 3027.0, 2969.3, 2361.3, 1744.3, 1716.1, 181.8, 1610.8, 1466.5, 1371.5, 1279.1, 1207.6, 1016.5, 760.0, 695.6 cm-1 HRMS (ESI) calcd for [M+H] C41H33N2O5, m/z: 633.2384, observed: 633.2378.

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