N-Trimethylsilyl Imines: Applications to the Synthesis of β-Lactams

Deok Chan Ha, David J. Hart, Teng Kuei Yang

Research output: Contribution to journalArticle

135 Citations (Scopus)

Abstract

Ester enolates and N-trimethylsilyl imines react to afford N-protio-β-lactams. The stereochemical course of the reaction depends on the ester enolate geometry. Therefore (E)-enolates give mainly cis β-lactams while (Z)-enolates give nearly equal mixtures of cis and trans β-lactams. The use of ethyl β-hydroxybutyrate as the ester component allows the preparation of β-lactams of potential use in carbapenem synthesis. The differences in the behavior of N-trimethylsilyl and N-aryl imines in ester-inline condensations are also discussed.

Original languageEnglish
Pages (from-to)4819-4825
Number of pages7
JournalJournal of the American Chemical Society
Volume106
Issue number17
DOIs
Publication statusPublished - 1984 Aug 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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