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Efficient Access to Isoxazoles from Alkenes

Jianping Xu, Ashton T. Hamme II*

*Department of Chemistry, Jackson State University, Jackson, MS 39217-0510, USA, Email:

J. Xu, A. T. Hamme II, Synlett, 2008, 919-923.

DOI: 10.1055/s-2008-1042906


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