Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes?

Chemical Communications Pub Date: 2011-02-01 DOI: 10.1039/C0CC04646A

Abstract

Treatment of oximes with hypervalent iodine leads to substituted isoxazolesvia rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure mild enough to prepare a range of nucleoside and peptide conjugates. Exceptionally high reaction rates were found for the formation of 3,4,5-trisubstituted isoxazoles from a cyclic alkyne.

Graphical abstract: Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes
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