Stereoselective synthesis of C3-tetrasubstituted oxindoles via copper catalyzed asymmetric propargylation.

Abstract

Herein, a copper catalyzed asymmetric propargylation of 2-oxindole-3-carboxylate esters with terminal propargylic esters is described. This strategy successfully provides a direct approach to constructing a broad range of chiral C3-tetrasubstituted oxindoles with contiguous tertiary and quaternary carbon stereocenters in high yields and excellent enantioselectivities (16 examples, up to 99% yield and 98% ee). Moreover, the diastereoisomers of the two newly formed stereocenters can be separated by silica gel chromatography, thereby providing a valuable stereoselective access to all four possible stereoisomers of C3-tetrasubstituted oxindoles.