N-trimethylsilyl imines: Applications to the synthesis of β-lactams

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

Research output: Contribution to journalArticle

134 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-imine condensations are also discussed.

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

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Lactams
Imines
Esters
Hydroxybutyrates
Carbapenems
Condensation
Geometry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

N-trimethylsilyl imines : Applications to the synthesis of β-lactams. / Ha, Deok-Chan; Hart, David J.; Yang, Teng Kuei.

In: Journal of the American Chemical Society, Vol. 106, No. 17, 01.12.1984, p. 4819-4825.

Research output: Contribution to journalArticle

Ha, Deok-Chan ; Hart, David J. ; Yang, Teng Kuei. / N-trimethylsilyl imines : Applications to the synthesis of β-lactams. In: Journal of the American Chemical Society. 1984 ; Vol. 106, No. 17. pp. 4819-4825.
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