Reduction of substituted. DELTA. 2-isoxazolines. Synthesis of. beta.-hydroxy acid derivatives

DP Curran, SA Scanga, CJ Fenk

Index: Curran, Dennis P.; Scanga, Susan A.; Fenk, Christopher J. Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3474 - 3478

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Citation Number: 72

Abstract

Three separate methods are reported for the formation of@-hydroxy acid derivatives from readily available substituted A2-isoxazolines. Cycloaddition of 2, 2-dimethylpropanenitrile oxide with a variety of olefins followed by reductive cleavage produces a'-tert-butyl@- hydroxy ketones. These are cleaved to@-hydroxy tert-butyl esters by Baeyer-Villiger oxidation with peroxytrifluoroacetic acid. In the second approach, a',@-dihydroxy ketones ...