Stereoselective nucleophilic addition to conformationally constrained piperidines. An efficient route to 2-axial-6-equatorial disubstituted piperidines.

A. I. Meyers; Thomas T. Shawe; Levi Gottlieb

doi:10.1016/s0040-4039(00)91562-4

Stereoselective nucleophilic addition to conformationally constrained piperidines. An efficient route to 2-axial-6-equatorial disubstituted piperidines.

A. I. Meyers
, Thomas T. Shawe
, Levi Gottlieb

Colorado State University

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

18 Scopus citations

Abstract

Addition of RMgX to 2-methoxy-4-tert-butylpiperidine formamidine in dichloromethane or ether gives good to excellent yields of axial product.

Original language	English
Pages (from-to)	867-870
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	7
DOIs	https://doi.org/10.1016/s0040-4039(00)91562-4
State	Published - 11 Feb 1992
Externally published	Yes

Bibliographical note

Funding Information:
In summary, nucleophilic alkylation on the methoxy epimers of 1 led to axial attack with good stereochemicalc ontrol and work is now in progress to evaluate other systems (e.g. 1A) as well as routes to aracemic products. Acknowledgement. Financial support by the National Science Foundation, and Merck Sharp and Dohme for a fellowship (to TTS) is gratefullya cknowledged.

Funding

In summary, nucleophilic alkylation on the methoxy epimers of 1 led to axial attack with good stereochemicalc ontrol and work is now in progress to evaluate other systems (e.g. 1A) as well as routes to aracemic products. Acknowledgement. Financial support by the National Science Foundation, and Merck Sharp and Dohme for a fellowship (to TTS) is gratefullya cknowledged.

Funders
National Science Foundation
Merck Sharp and Dohme

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10.1016/s0040-4039(00)91562-4

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title = "Stereoselective nucleophilic addition to conformationally constrained piperidines. An efficient route to 2-axial-6-equatorial disubstituted piperidines.",

abstract = "Addition of RMgX to 2-methoxy-4-tert-butylpiperidine formamidine in dichloromethane or ether gives good to excellent yields of axial product.",

author = "Meyers, \{A. I.\} and Shawe, \{Thomas T.\} and Levi Gottlieb",

note = "Funding Information: In summary, nucleophilic alkylation on the methoxy epimers of 1 led to axial attack with good stereochemicalc ontrol and work is now in progress to evaluate other systems (e.g. 1A) as well as routes to aracemic products. Acknowledgement. Financial support by the National Science Foundation, and Merck Sharp and Dohme for a fellowship (to TTS) is gratefullya cknowledged.",

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doi = "10.1016/s0040-4039(00)91562-4",

language = "אנגלית",

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AU - Meyers, A. I.

AU - Shawe, Thomas T.

AU - Gottlieb, Levi

N1 - Funding Information: In summary, nucleophilic alkylation on the methoxy epimers of 1 led to axial attack with good stereochemicalc ontrol and work is now in progress to evaluate other systems (e.g. 1A) as well as routes to aracemic products. Acknowledgement. Financial support by the National Science Foundation, and Merck Sharp and Dohme for a fellowship (to TTS) is gratefullya cknowledged.

PY - 1992/2/11

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N2 - Addition of RMgX to 2-methoxy-4-tert-butylpiperidine formamidine in dichloromethane or ether gives good to excellent yields of axial product.

AB - Addition of RMgX to 2-methoxy-4-tert-butylpiperidine formamidine in dichloromethane or ether gives good to excellent yields of axial product.

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IS - 7

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Stereoselective nucleophilic addition to conformationally constrained piperidines. An efficient route to 2-axial-6-equatorial disubstituted piperidines.

Abstract

Bibliographical note

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