Iron catalyzed efficient synthesis of poly-functional primary amines via the direct use of ammonia

Abstract

An iron catalyzed three-component reaction of alkyl diazoesters, isatins and ammonia is reported. This reaction provided convenient access to non-protected β-hydroxy-α-aminoesters with adjacent quaternary stereocenters. This transformation is achieved via trapping of ammonium ylide which is generated from a diazocompound and ammonia under mild reaction conditions. Poly-functional group unprotected amines are obtained exclusively with up to 77% yield and 62 : 38 dr.