Enantioselective Vinylogous Mukaiyama‐Michael Reaction of Silyl Ketene Acetals to α,β‐Unsaturated 2‐Acyl Imidazoles to Construct 1,7‐dioxo Compounds

Abstract

The synthesis of chiral 1,7‐dioxo compounds via Sc(III)‐pybox catalyzed vinylogous Mukaiyama‐Michael reaction of vinyl ketene silyl acetals with α,β‐unsaturated 2‐acyl imidazoles has been described. This innovative approach to the formation of chiral 1,7‐dioxo compounds illustrates excellent regio‐, and enantioselectivities, demonstrating a broad substrate scope. So far, to the best of our knowledge, this is the first example of a metal‐catalyzed asymmetric vinylogous Mukaiyama‐Michael reaction using vinyl ketene silyl acetals.