Compound 3a

(3S,3''S,2'R,5'S)-1-Acetyl-1''-benzyl-dispiro[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

View in PubChem | MDL Molfile | ChemDraw

InChIKey ASYBXOJAHWOCKD-QYSAAILDSA-N

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

The multifunctional catalyst VIII (0.01 mmol, 0.2 equiv) was added to a solution of 3-substituted oxindole 1a (0.05 mmol, 1.0 equiv) and methyleneindolinone ester 2a (0.075 mmol, 1.5 equiv) in DCM (0.2 mL) at room temperature (23 °C). After 24 hours, the product 3a was afforded by silica gel flash column chromatography using gradient elution (EtOAc/Hexane = 1:10 to 1:8). 1H-NMR (500 MHz, CDCl3) δ 8.18 (d, J = 7.0 Hz, 1H), 8.04 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 7.0 Hz, 1H), 7.38-7.29 (m, 7H), 7.25-7.22 (m, 1H), 7.19-7.16 (m, 2H), 7.11 (t, J = 8.0 Hz, 2H), 7.02 (d, J = 7.5 Hz, 2H), 6.92 (s, 1H), 6.79 (d, J = 7.5 Hz, 1H), 5.32 (d, J = 16.0 Hz, 1H), 4.84 (d, J = 15.5 Hz, 1H), 4.55 (s, 1H), 4.29 (d, J = 14.5 Hz, 1H), 2.92 (s, 3H), 2.58 (d, J = 14.0 Hz, 1H), 2.42 (s, 3H). 13C-NMR (100 MHz, CDCl3) δ 183.91, 177.90, 170.82, 169.01, 142.89, 141.18, 137.57, 135.34, 131.85, 129.61, 129.28, 129.12, 128.65, 128.36, 128.00, 127.43, 126.08, 125.92, 124.95, 124.57, 116.20, 109.84, 85.85, 67.87, 62.29, 54.70, 51.98, 26.06, 44.81, 26.75. HPLC: Chiralpak AD-H (hexane/i-PrOH = 90/10, flow rate 2 mL/min, λ = 254 nm), tR (minor) = 8.4 min, tR (major) = 18.0 min; 95:5 er. [α]D25 = +91.5 (c = 0.4, CH2Cl2). IR (CH2Cl2) ν 3285.1, 2913.9, 2359.1, 1707.6, 1684.8, 1611.0, 1466.7, 1276.8, 1171.5, 756.5 cm-1. HRMS (ESI) calcd for [M+H] C36H30N2O6, m/z: 587.2177, observed: 587.2159.

Back to article page