Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

Junyi Zhang; Wei Wang; Chiyi Xiong; Victor J Hruby

doi:10.1016/S0040-4039(02)02865-4

Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

Junyi Zhang
, Wei Wang
, Chiyi Xiong
, Victor J Hruby

Chemistry and Biochemistry

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

19 Scopus citations

Abstract

A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the γ-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity.

Original language	English (US)
Pages (from-to)	1413-1415
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4039(02)02865-4
State	Published - Feb 10 2003

Keywords

Alkylation
Constrained amino acids
Proline

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)02865-4

Cite this

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title = "Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues",

abstract = "A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the γ-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity.",

keywords = "Alkylation, Constrained amino acids, Proline",

author = "Junyi Zhang and Wei Wang and Chiyi Xiong and Hruby, \{Victor J\}",

note = "Funding Information: This work was supported by US Public Health Service (DK 17420) and the National Institute of Drug Abuse (DA 13449). We thank Professor Dominic V. McGrath for the use of his group's polarimeter. The opinions expressed are those of the authors and not necessarily those of the US Public Health Service.",

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T1 - Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

AU - Zhang, Junyi

AU - Wang, Wei

AU - Xiong, Chiyi

AU - Hruby, Victor J

N1 - Funding Information: This work was supported by US Public Health Service (DK 17420) and the National Institute of Drug Abuse (DA 13449). We thank Professor Dominic V. McGrath for the use of his group's polarimeter. The opinions expressed are those of the authors and not necessarily those of the US Public Health Service.

PY - 2003/2/10

Y1 - 2003/2/10

N2 - A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the γ-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity.

AB - A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the γ-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity.

KW - Alkylation

KW - Constrained amino acids

KW - Proline

UR - https://www.scopus.com/pages/publications/0037429021

UR - https://www.scopus.com/pages/publications/0037429021#tab=citedBy

U2 - 10.1016/S0040-4039(02)02865-4

DO - 10.1016/S0040-4039(02)02865-4

M3 - Article

AN - SCOPUS:0037429021

SN - 0040-4039

VL - 44

SP - 1413

EP - 1415

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

Abstract

Keywords

ASJC Scopus subject areas

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