A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones

V. A. Soloshonok, C. Cai, V. J. Hruby

Research output: Contribution to journalArticle

68 Scopus citations

Abstract

The origin of virtually complete face diastereoselectivity in the organic base-catalyzed, room temperature Michael addition reactions between Ni(II)-complexes of Schiff bases of glycine and chiral 3-(E-enoyl)-4-substituted-1,3-oxazolidin-2-ones was shown to stem from the unusual mode of steric interactions in determining the corresponding transition state. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)9645-9649
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number49
DOIs
StatePublished - Dec 2 2000

Keywords

  • Amino acids
  • Asymmetric synthesis
  • Michael additions
  • Nickel(II) complex
  • Oxazolidin-2-ones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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