Organocatalytic asymmetric synthesis of functionalized 1,3,5- triarylpyrrolidin-2-ones via an aza-Michael/aldol domino reaction

Abstract

The organocatalytic asymmetric synthesis of functionalized 1,3,5-triarylpyrrolidin-2-ones bearing three contiguous stereocenters through an aza-Michael/aldol domino reaction of α-ketoamides with α,β-unsaturated aldehydes is described. The domino products were further derivatized by aldehyde olefination under one-pot conditions. The reaction proceeds with excellent diastereoselectivities (>20:1) and good to excellent enantioselectivities (60-96% ee). © Georg Thieme Verlag Stuttgart · New York.