Highly Efficient and Regioselective Synthesis of N‐Acyl Protected 2‐Aminoacrylates through a PPh3‐Catalyzed Reaction of Alkyl Propiolates with Amides

Abstract

AbstractA simple and convenient strategy for the synthesis of N‐acyl protected 2‐aminoacrylates via PPh3‐catalyzed reaction of alkyl propiolates with amides has been developed. This protocol is rapid and highly regioselective to provide various N‐acyl protected 2‐aminoacrylates in high yields (up to 95 %). The chemical structure of the product was determined by X‐ray single‐crystal structure analysis. In contrast, 3‐sulfonamidoacrylates were obtained by Cs2CO3‐catalyzed reactions of alkyl propiolates with secondary sulfamides. Moreover, synthetic utility of this method was further highlighted in the late‐stage modification of drug molecules.