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

Bryce Sunsdahl; Adrian R. Smith; Tom Livinghouse

doi:10.1002/anie.201407768

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

Bryce Sunsdahl, Adrian R. Smith, Tom Livinghouse

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

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.

Original language	English (US)
Pages (from-to)	14352-14356
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	52
DOIs	https://doi.org/10.1002/anie.201407768
State	Published - Dec 22 2014

Bibliographical note

Publisher Copyright:
© 2014 Wiley-VCH Verlag GmbH & Co. KGaA , Weinheim.

Keywords

Cyclization
Hydrazines
Metalloamination
Nitrogen heterocycles
Organozinc compounds

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10.1002/anie.201407768

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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.",

keywords = "Cyclization, Hydrazines, Metalloamination, Nitrogen heterocycles, Organozinc compounds",

author = "Bryce Sunsdahl and Smith, {Adrian R.} and Tom Livinghouse",

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T1 - Intramolecular metalloamination of N,N-dimethylhydrazinoalkenes

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AU - Smith, Adrian R.

AU - Livinghouse, Tom

PY - 2014/12/22

Y1 - 2014/12/22

N2 - 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.

AB - 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.

KW - Cyclization

KW - Hydrazines

KW - Metalloamination

KW - Nitrogen heterocycles

KW - Organozinc compounds

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M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

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

Abstract

Bibliographical note

Keywords

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