Copper Induced Cyclization of α,β-Unsaturated Carbonyl Compounds to Isoxazoles

Title: Copper Induced Cyclization of α,β-Unsaturated Carbonyl Compounds to Isoxazoles

Volume: 8 Issue: 4

Author(s): Cindy C. Browder, Christopher B. Moss, Matthew B. Kraft, Paige L. Petrucka, Tara S. Morey, Christopher W. Leach and Nicholas C. Gearhart

Affiliation:

Keywords: Isoxazole, cyclization, copper-mediated, antiinflammatory, pharmaceuticals, antibiotic, ketoxime, anhydrous, Beckmann rearrangement, olefin-tethered substrate

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.

Cite this article as:

C. Browder Cindy, B. Moss Christopher, B. Kraft Matthew, L. Petrucka Paige, S. Morey Tara, W. Leach Christopher and C. Gearhart Nicholas, Copper Induced Cyclization of α,β-Unsaturated Carbonyl Compounds to Isoxazoles, Letters in Organic Chemistry 2011; 8 (4) . https://dx.doi.org/10.2174/157017811795371476