Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions

Chaozhong Cai; Takeshi Yamada; Rohit Tiwari; Victor J. Hruby; Vadim A. Soloshonok

doi:10.1016/j.tetlet.2004.07.096

Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions

Chaozhong Cai, Takeshi Yamada, Rohit Tiwari, Victor J. Hruby, Vadim A. Soloshonok

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

31 Scopus citations

Abstract

Methyl N-(E-enoyl)pyroglutamates, derived from inexpensive and readily available in both enantiomeric forms pyroglutamic acid were found to be an efficient Michael acceptors in the addition reactions with nucleophilic glycine equivalent allowing for an efficient practical asymmetric synthesis of β-substituted pyroglutamic acids and related compounds.

Original language	English (US)
Pages (from-to)	6855-6858
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2004.07.096
State	Published - Sep 6 2004
Externally published	Yes

Keywords

Asymmetric synthesis
Michael addition
Ni(II)-complex
Pyroglutamate

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.07.096

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title = "Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions",

abstract = "Methyl N-(E-enoyl)pyroglutamates, derived from inexpensive and readily available in both enantiomeric forms pyroglutamic acid were found to be an efficient Michael acceptors in the addition reactions with nucleophilic glycine equivalent allowing for an efficient practical asymmetric synthesis of β-substituted pyroglutamic acids and related compounds.",

keywords = "Asymmetric synthesis, Michael addition, Ni(II)-complex, Pyroglutamate",

author = "Chaozhong Cai and Takeshi Yamada and Rohit Tiwari and Hruby, {Victor J.} and Soloshonok, {Vadim A.}",

note = "Funding Information: The work was supported by the start-up fund provided by the Department of Chemistry and Biochemistry, University of Oklahoma (to V.A.S.), and by the grants from US Public Health Service Grant and the National Institute of Drug Abuse (DA 06284, DA 04248, and DK 17420 to V.J.H.). ",

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doi = "10.1016/j.tetlet.2004.07.096",

language = "English (US)",

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TY - JOUR

T1 - Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions

AU - Cai, Chaozhong

AU - Yamada, Takeshi

AU - Tiwari, Rohit

AU - Hruby, Victor J.

AU - Soloshonok, Vadim A.

N1 - Funding Information: The work was supported by the start-up fund provided by the Department of Chemistry and Biochemistry, University of Oklahoma (to V.A.S.), and by the grants from US Public Health Service Grant and the National Institute of Drug Abuse (DA 06284, DA 04248, and DK 17420 to V.J.H.).

PY - 2004/9/6

Y1 - 2004/9/6

N2 - Methyl N-(E-enoyl)pyroglutamates, derived from inexpensive and readily available in both enantiomeric forms pyroglutamic acid were found to be an efficient Michael acceptors in the addition reactions with nucleophilic glycine equivalent allowing for an efficient practical asymmetric synthesis of β-substituted pyroglutamic acids and related compounds.

AB - Methyl N-(E-enoyl)pyroglutamates, derived from inexpensive and readily available in both enantiomeric forms pyroglutamic acid were found to be an efficient Michael acceptors in the addition reactions with nucleophilic glycine equivalent allowing for an efficient practical asymmetric synthesis of β-substituted pyroglutamic acids and related compounds.

KW - Asymmetric synthesis

KW - Michael addition

KW - Ni(II)-complex

KW - Pyroglutamate

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DO - 10.1016/j.tetlet.2004.07.096

M3 - Article

AN - SCOPUS:4344655353

SN - 0040-4039

VL - 45

SP - 6855

EP - 6858

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions

Abstract

Keywords

ASJC Scopus subject areas

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