Selective Ruthenium-Catalyzed Oxidation of 1,2:4,5-Di-<i>O</i>-isopropylidene- β-d-fructopyranose and Other Alcohols with NaOCl

The asymmetric epoxidation catalyst 1,2:4,5-di-O-isopropylidene-β-d-erythro-2,3-hexadiulo-2,6-pyranose 2 was obtained in high yield from 1,2:4,5-di-O-isopropylidene-β-d-fructopyranose 1 via a recyclable ruthenium-catalyzed hypochlorite oxidation protocol under biphasic conditions (MTBE/water) in the presence of an alkaline buffer (pH 9.5). Other secondary alcohols were also oxidized selectively to the corresponding ketones.