Intramolecular metalloamination of N,N-dimethylhydrazinoalkenes: A versatile method to access functionalized piperidines and pyrrolidines

Abstract

Highly diastereoselective metalloamination/cyclization reactions of zinc(II) hydrazides obtained through reaction of diethylzinc with N,N-dimethylhydrazinoalkenes are described.The resulting organozinc intermediates undergo facile allylation and acylation, in situ, to provide the corresponding functionalized piperidines and pyrrolidines.