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 journalArticle

76 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2172-2175
Number of pages4
JournalAngewandte Chemie - International Edition
Volume39
Issue number12
DOIs
StatePublished - Jun 16 2000

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Pyrrolidonecarboxylic Acid
Oxazolidinones
Addition reactions
Schiff Bases
Nickel
Glycine
Amino acids
Acids
Temperature

Keywords

  • Amino acids
  • Asymmetric synthesis
  • Michael additions
  • Nickel

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds. / Soloshonok, Vadim A.; Cai, Chaozhong; Hruby, Victor J.

In: Angewandte Chemie - International Edition, Vol. 39, No. 12, 16.06.2000, p. 2172-2175.

Research output: Contribution to journalArticle

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