Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

Cindy C. Browder, Christopher B. Moss, Matthew B. Kraft, Paige L. Petrucka, Tara S. Morey, Christopher W. Leach, Nicholas C. Gearhart

Research output: Contribution to journalArticle

Abstract

An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

Original languageEnglish (US)
Pages (from-to)229-233
Number of pages5
JournalLetters in Organic Chemistry
Volume8
Issue number4
DOIs
StatePublished - May 1 2011

Keywords

  • Copper-mediated
  • Cyclization
  • Isoxazole

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles'. Together they form a unique fingerprint.

  • Cite this

    Browder, C. C., Moss, C. B., Kraft, M. B., Petrucka, P. L., Morey, T. S., Leach, C. W., & Gearhart, N. C. (2011). Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles. Letters in Organic Chemistry, 8(4), 229-233. https://doi.org/10.2174/157017811795371476