Electroreductive Ring Opening ofa,b-Epoxy Carbonyl Compounds and Their Homologues though Recyclable Use of Diphenyl Diselenide or Diphenyl Ditelluride as a Mediator

Inokuchi, T.; Kusumoto, M.; Torii, S. J. Org. Chem. 1990, 55, 1548.

A novel access to b-hydroxy carbonyl compounds from the corresponding a,b-epoxy carbonyl compounds has been attained through the recyclable use of diphenyl diselenide or diphenyl ditelluride as an electro-reduction mediator in a MeOH-NaClO₄-(Pt) system. a,b-Epoxy ketones are converted to the corresponding aldols in the presence of malonic esters. Similarly,a,b-epoxy esters and nitriles can be reduced to the corresponding b-hydroxy compounds in the presence of acetic acid.