Sequential nitromethane conjugate addition/elimination - Pd-catalyzed allylation of β-trifloxy acrylates. Application to carbapenem synthesis

John Y.L. Chung, Edward J.J. Grabowski, Paul J. Reider

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

(formula presented) Sequential reactions of nitromethane via conjugate addition - elimination to B-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the β-position. 2-Naphthosultammethyl carbapenem, pan anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.

Original languageEnglish (US)
Pages (from-to)1783-1785
Number of pages3
JournalOrganic Letters
Volume1
Issue number11
DOIs
StatePublished - Dec 2 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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