A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters

Jiro Tsuji, Kiyomi Sakai, Hideo Nagashima, Isao Shimizu

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

A new synthetic method for γ-acetoxy-α,β-unsaturated esters by the acetoxylation of β,γ-unsaturated esters catalyzed by PdCl2 in the presence of KOAc and pentyl nitrite in acetic acid is presented. The reaction takes place at γ-position of the esters regioselectively with double bond migration to α,β-position. The E configuration of the double bond was confirmed by NMR analysis. Preliminary investigation to synthesize pyrenophorin and pyrenophorol using this reaction is described.

Original languageEnglish
Pages (from-to)131-134
Number of pages4
JournalTetrahedron Letters
Volume22
Issue number2
DOIs
Publication statusPublished - Jan 1 1981
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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