Intramolecular Metalloamination of N,N-dimethylhydrazinoalkenes: a Versatile Method to Access Functionalized Piperidines and Pyrrolidines

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2014 Oct 11

PMID 25302713

Citations 4

Authors

Bryce Sunsdahl

Adrian R Smith

Tom Livinghouse

Affiliations

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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.

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