Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors

The direct Mukaiyama-Michael addition of vinylogous tetramate donors to a number of different Michael acceptors has been easily executed, by employing the TMSOTf/Et3N Mixture as soft Lewis acid/base promoter agent. Richly functionalized, highly manipulable gamma-substituted pyrrolinone products were practically synthesized in acceptable to excellent yields, and with diastereoselectivities heavily relying upon the substituent at the nitrogen atom of the pyrrolinone donor. (C) 2008 Elsevier Ltd. All rights reserved.