Stereoselective dioxygenation of enoates

Patrick H. Dussault, Kevin R. Woller, Michael C. Hillier

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

The auxiliary-directed reaction of singlet oxygen with tiglate esters furnishes an asymmetric synthesis of 3-hydroperoxy-2-methylidene butenoates. Although previous reports have suggested that s-cis enoate conformers undergo preferential oxygenation relative to the s-trans conformers, our results suggest that both conformers are reactive and that the modest stereoselectivity is based upon a conformational equilibrium favoring the s-trans conformer.

Original languageEnglish (US)
Pages (from-to)8929-8940
Number of pages12
JournalTetrahedron
Volume50
Issue number30
DOIs
StatePublished - 1994

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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