Catalytic stereospecific allylation of protected hydrazines with enantioenriched primary allylic amines

Abstract

An unprecedented allylation reaction of protected hydrazines with enantioenriched allylic amines has been developed in a stereospecific manner with net stereoretention. A wide variety of protected hydrazines underwent palladium/acid-catalyzed allylation with highly enantioenriched primary allylic amines to give structurally diverse N-allylhydrazines in moderate to excellent yields with extremely high regioselectivity and complete retention of the configuration. Importantly, the reaction exhibits high atom-economy by yielding ammonia as the sole byproduct.