Electroreductive ring-opening of. alpha.,. beta.-epoxy carbonyl compounds and their homologs through recyclable use of diphenyl diselenide or diphenyl ditelluride as …

T Inokuchi, M Kusumoto, S Torii

Index: Inokuchi, Tsutomu; Kusumoto, Masahiko; Torii, Sigeru Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1548 - 1553

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Citation Number: 44

Abstract

A novel access to@-hydroxy carbonyl compounds from the corresponding a,@-epoxy carbonyl compounds has been attained through the recyclable use of diphenyl diselenide or diphenyl ditelluride as an electroreduction mediator in a MeOH-NaClO,-(Pt) system. a,@- Epoxy ketones are converted to the corresponding aldols in the presence of malonic esters. Similarly, a,@-epoxy esters and nitriles can be reduced to the corresponding@-hydroxy ...