SN2-type ring opening of substituted-N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt

Abstract

Quaternary ammonium salt mediated highly regioselective ring opening of aziridines with zinc(II) halides to racemic and non-racemic β-halo amines in excellent yield and selectivity is described. The reaction proceeds via an SN2-type pathway and the partial racemization of the starting substrate and the product was effectively controlled by using quaternary ammonium salts to afford the enantioenriched products (er up to 95:5). © Indian Academy of Sciences.