Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

…, BJ Kastern, SR Koski, AV Maskaev, VV Zhdankin

Index: Yoshimura, Akira; Middleton, Kyle R.; Todora, Anthony D.; Kastern, Brent J.; Koski, Steven R.; Maskaev, Andrey V.; Zhdankin, Viktor V. Organic Letters, 2013 , vol. 15, # 15 p. 4010 - 4013

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Citation Number: 61

Abstract

Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.