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

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

Keywords

  • Amino acids
  • Asymmetric synthesis
  • Michael additions
  • Nickel

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds'. Together they form a unique fingerprint.

  • Cite this