Organocatalytic tandem three-component reaction of imine, alkyl vinyl ketone, and imide via aza-Baylis-Hillman reaction

J Org Chem. 2011 Apr 15;76(8):2888-91. doi: 10.1021/jo102143r. Epub 2011 Mar 14.

Abstract

A highly chemoselective PPh(3)-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide is developed. Various highly functional adducts with high diastereoselectivities can be generated via aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl ketones followed by Michael additions of imides and then epimerization.