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Highly diastereo- and enantioselective Michael additions of 3-substituted oxindoles to maleimides catalyzed by chiral bifunctional thiourea-tertiary amine.

Research paper by Yu-Hua YH Liao, Xiong-Li XL Liu, Zhi-Jun ZJ Wu, Lin-Feng LF Cun, Xiao-Mei XM Zhang, Wei-Cheng WC Yuan

Indexed on: 10 Jun '10Published on: 10 Jun '10Published in: Organic Letters



Abstract

A highly diastereo- and enantioselective Michael addition reaction with respect to prochiral 3-substituted oxindoles and maleimides by a chiral bifunctional thiourea-tertiary amine catalyst was investigated for the first time. The corresponding adducts, containing a quaternary center at the C3-position of the oxindole as well as a vicinal tertiary center, were generally obtained in good to high yields (up to 92%) with high to excellent diastereo- (up to 99:1 dr) and enantioselectivities (up to 99% ee).