Asymmetric Construction of Quaternary Carbon Stereocenters:  High Stereoselection in Mukaiyama Aldol Reactions of 2-Siloxyindoles with Chiral Aldehydes

Abstract

[reaction: see text] A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aldehydes having nitrogen or oxygen substituents at the alpha carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1).