Copper-catalyzed rearrangement of vinyl oxiranes

Lindsay A. Batory, Christine E. McInnis, Jon T. Njardarson

Research output: Contribution to journalArticle

53 Scopus citations

Abstract

A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.

Original languageEnglish (US)
Pages (from-to)16054-16055
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number50
DOIs
StatePublished - Dec 20 2006
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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