Organocatalytic Ring-opening Reactions of Cyclopropenones with Amines

Abstract

Due to the ubiquitous nature of amide bonds, amidation reaction is recognized as one of the key transformations in organic synthesis. Recently, the synthesis of tri-substituted enamides has gained much importance due to the associated biological activities of the motif. However, their synthetic routes are plagued by the requirement of chlorinating agents, expensive transition-metal catalysts, and harsh reaction conditions. Keeping the high requirement and industrial usage of amidation reactions, coupled with the poor atom economy of current methodologies, we describe an organocatalytic method for the N-acylation of amines with cyclopropenones to access α,β-unsaturated amides, using 4-N,N-dimethylaminopyridine (DMAP) as a catalyst.