A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds

Vadim A. Soloshonok; Chaozhong Cai; Victor J. Hruby

doi:10.1002/1521-3773(20000616)39:12<2172::AID-ANIE2172>3.0.CO;2-0

A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds

Vadim A. Soloshonok, Chaozhong Cai, Victor J. Hruby

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

86 Scopus citations

Abstract

DBU-catalyzed Michael addition reactions were shown to occur at room temperature between a nickel(II) complex of the Schiff base of glycine 1 and (S)- or (R)-N-(E-enoyl)-4-phenyl-3-oxazolidin-2-ones (2, see scheme). This reaction, which has an almost completely stereoselective outcome, provides a practical and generalized approach to a family of glutamic/pyroglutamic acids. R = alkyl, aryl.

Original language	English (US)
Pages (from-to)	2172-2175
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	12
DOIs	https://doi.org/10.1002/1521-3773(20000616)39:12<2172::AID-ANIE2172>3.0.CO;2-0
State	Published - Jun 16 2000
Externally published	Yes

Keywords

Amino acids
Asymmetric synthesis
Michael additions
Nickel

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/1521-3773(20000616)39:12<2172::AID-ANIE2172>3.0.CO;2-0

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keywords = "Amino acids, Asymmetric synthesis, Michael additions, Nickel",

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

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T1 - A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds

AU - Soloshonok, Vadim A.

AU - Cai, Chaozhong

AU - Hruby, Victor J.

PY - 2000/6/16

Y1 - 2000/6/16

N2 - DBU-catalyzed Michael addition reactions were shown to occur at room temperature between a nickel(II) complex of the Schiff base of glycine 1 and (S)- or (R)-N-(E-enoyl)-4-phenyl-3-oxazolidin-2-ones (2, see scheme). This reaction, which has an almost completely stereoselective outcome, provides a practical and generalized approach to a family of glutamic/pyroglutamic acids. R = alkyl, aryl.

AB - DBU-catalyzed Michael addition reactions were shown to occur at room temperature between a nickel(II) complex of the Schiff base of glycine 1 and (S)- or (R)-N-(E-enoyl)-4-phenyl-3-oxazolidin-2-ones (2, see scheme). This reaction, which has an almost completely stereoselective outcome, provides a practical and generalized approach to a family of glutamic/pyroglutamic acids. R = alkyl, aryl.

KW - Amino acids

KW - Asymmetric synthesis

KW - Michael additions

KW - Nickel

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DO - 10.1002/1521-3773(20000616)39:12<2172::AID-ANIE2172>3.0.CO;2-0

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds

Abstract

Keywords

ASJC Scopus subject areas

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