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 2011

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Isoxazoles
Carbonyl compounds
Oximes
Cyclization
Copper
Isomers

Keywords

  • Copper-mediated
  • Cyclization
  • Isoxazole

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

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

Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles. / Browder, Cindy C; Moss, Christopher B.; Kraft, Matthew B.; Petrucka, Paige L.; Morey, Tara S.; Leach, Christopher W.; Gearhart, Nicholas C.

In: Letters in Organic Chemistry, Vol. 8, No. 4, 05.2011, p. 229-233.

Research output: Contribution to journalArticle

Browder, CC, Moss, CB, Kraft, MB, Petrucka, PL, Morey, TS, Leach, CW & Gearhart, NC 2011, 'Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles', Letters in Organic Chemistry, vol. 8, no. 4, pp. 229-233. https://doi.org/10.2174/157017811795371476
Browder, Cindy C ; Moss, Christopher B. ; Kraft, Matthew B. ; Petrucka, Paige L. ; Morey, Tara S. ; Leach, Christopher W. ; Gearhart, Nicholas C. / Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles. In: Letters in Organic Chemistry. 2011 ; Vol. 8, No. 4. pp. 229-233.
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