A Metal-Catalyzed Tunable Reaction of Ylides with Hydroxylamine Derivatives

Abstract

In this work, a tunable reaction of metal acyl nitrene with ylides is reported for the divergent synthesis of enamides and α,α-dicarbonyl phosphorus ylides. The reaction is featured with mild conditions, good reaction efficiency, and broad reaction generality. In particular, the resulting enamides could be structurally elaborated into potential useful scaffolds. Mechanism investigation suggests that the formation of enamides was ascribed to the nucleophilic substitution of ferric nitrene with sulfur ylides. It is believed that this reaction represents an initial example of preparing enamides from iron-catalyzed nitrene transfer.