title: 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.
authors.affiliation: Department of Chemistry and Biochemistry, 103 CBB, Montana State University, Bozeman, MT 59717 (USA).
authors.forename: Bryce
authors.initials: B
authors.lastname: Sunsdahl
authors.forename: Adrian R
authors.initials: AR
authors.lastname: Smith
authors.forename: Tom
authors.initials: T
authors.lastname: Livinghouse
keywords: cyclization; hydrazines; metalloamination; nitrogen heterocycles; organozinc compounds