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

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

18 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
Externally published	Yes

Bibliographical note

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

Keywords

Cyclization
Hydrazines
Metalloamination
Nitrogen heterocycles
Organozinc compounds

Access

10.1002/anie.201407768

OpenUrl availability

Full text

Cite this

@article{72a9d644195a41d78da47e722d0f153f,

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.",

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

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

note = "Publisher Copyright: {\textcopyright} 2014 Wiley-VCH Verlag GmbH & Co. KGaA , Weinheim.",

year = "2014",

month = dec,

day = "22",

doi = "10.1002/anie.201407768",

language = "English (US)",

volume = "53",

pages = "14352--14356",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "52",

}

TY - JOUR

T1 - Intramolecular metalloamination of N,N-dimethylhydrazinoalkenes

T2 - A versatile method to access functionalized piperidines and pyrrolidines

AU - Sunsdahl, Bryce

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

UR - http://www.scopus.com/inward/record.url?scp=84919609012&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84919609012&partnerID=8YFLogxK

U2 - 10.1002/anie.201407768

DO - 10.1002/anie.201407768

M3 - Article

AN - SCOPUS:84919609012

SN - 1433-7851

VL - 53

SP - 14352

EP - 14356

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 52

ER -

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

Abstract

Bibliographical note

Keywords

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this