Electroreductive Deoxygenation of Methanesulfonates of a-Hydroxy Esters via a Catalytic Selenation-Deselenation Sequence

Inokuchi, T.; Sugimoto, T.; Kusumoto, M.; Torii, S. Bull. Chem. Soc. Jpn. 1992, 65, 3200.

The methanesulfonated of a-hydoxy esters were converted to the corresponding deoxygenated esters in 70-88% yields by the indirect electrolysis with diphenyl diselenide as a recyclable reagent in a divided cell. This deoxygenation method may involve the formation of a-phenylselenoester by replacement of a-methylsulfonyloxyl group with phenylselenide anion followed by capture of the a-phenylseleno group with phenylselenide anion.