Efficient Access to Isoxazoles from Alkenes
Jianping Xu, Ashton T. Hamme II*
*Department of Chemistry, Jackson State University, Jackson,
MS 39217-0510, USA,
Email: ashton.t.hamme
jsums.edu
J. Xu, A. T. Hamme II, Synlett, 2008, 919-923.
DOI: 10.1055/s-2008-1042906
Abstract
The direct regioselective synthesis of 3,5-disubstituted isoxazoles was achieved through a sequence involving a net bromination of an electron-deficient alkene, in situ generation of a nitrile oxide, 1,3-dipolar cycloaddition, and loss of HBr from an intermediate bromoisoxazoline. This one-pot process enables the direct synthesis of 3,5-disubstituted isoxazoles from electron-deficient alkenes.
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Key Words
dipolar cycloadditions, heterocycles, isoxazoles, tandem reactions, alkyne surrogate, dehydrohalogenation
ID: J60-Y2008-0940
