N-Heterocyclic Carbene-Catalyzed Generation of α,β-Unsaturated Acyl Imidazoliums: Synthesis of Dihydropyranones by their Reaction with Enolates

Abstract

Catalytic generation of alpha,beta-unsaturated acyl imidazolium cations and enolates has been achieved, and their involvement in a Michael addition acylation sequence exploited, to provide a range of dihydropyranones. alpha,beta-Unsaturated enol esters, or alpha,beta-unsaturated acid fluorides in association with TMS enol ethers, serve as appropriate substrates for this reaction. The transformation can also be achieved enantioselectively using catalysts derived from chiral triazolium salts.