Organocatalytic Direct Asymmetric Vinylogous Michael Reaction of an α,β-Unsaturated γ-Butyrolactam with Enones

Abstract

An organocatalytic asymmetric direct vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to enones has been achieved with a simple bifunctional thiourea-tertiary amine catalyst, affording the γ-substituted butyrolactam products with high diastereo- and enantioselectivity (up to >40:1 dr and 94-99% ee).