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Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines

Organic & Biomolecular ChemistryPublished 1 January 2014
Zhongkai Tang, Yan Shi, Haibin Mao, Xuebin Zhu, Weipeng Li, Yixiang Cheng
Citations49
SJR quartileQ2
SJR score0.60
SNIP0.71

TL;DR

A highly efficient asymmetric organocatalytic addition of 3-substituted oxindole to isatin-derived ketimine is reported with excellent stereocontrol under mild conditions and provides access to the bisoxindole structure moiety with two vicinal quaternary stereogenic centers.

Abstract

A highly efficient asymmetric organocatalytic addition of 3-substituted oxindole to isatin-derived ketimine is reported with excellent stereocontrol (>99 : 1 dr, >99% ee) under mild conditions. This method provides access to the bisoxindole structure moiety with two vicinal quaternary stereogenic centers.

Keywords

Chemistry