Mukaiyama–Michael reaction: enantioselective strategies and applications in total synthesis

Abstract

The Mukaiyama–Michael (M–M) reaction is a powerful approach for carbon–carbon bond formation and can provide access to all-carbon quaternary centers and vicinal stereocenters. The use of chiral catalysts for this transformation has enabled the development of efficient asymmetric methods in which the reaction proceeds with high enantioselectivity in the presence of only a substoichiometric amount of the chiral promoter. Both chiral Lewis acid catalysts and organocatalysts have been employed. These catalytic methods have afforded improvements in reactivity, selectivity, and substrate scope for the M–M reaction and have enabled the synthesis of complex molecular targets including natural products. In this review, enantioselective M–M methods are surveyed along with their applications in the total synthesis of natural products.