A highly stereoselective synthesis of a key intermediate of 1β-methylcarbapenems employing the reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives

Yoshio Ito, Shiro Terashima

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Reaction of sterically crowded achiral 3-(2-bromopropionyl)-2-oxazolidone derivatives with (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone in the presence of zinc dust in refluxing tetrahydrofuran was found to give the 1β-methyl substituted β-lactams as major products (at most, β:α=95:5). The major products were readily converted into the key intermediate of 1β-methylcarbapenems.

Original languageEnglish
Pages (from-to)6625-6628
Number of pages4
JournalTetrahedron Letters
Volume28
Issue number52
DOIs
Publication statusPublished - 1987
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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