Heterogeneous copper-catalyzed direct reduction of C-glycosidic enones to saturated alcohols in water

Abstract

We report a novel method for the reduction of α,β-unsaturated enones to the corresponding fully saturated alcohols in a single procedure. Remarkably, the method employs a heterogeneous copper catalyst in water and only requires resin-treatment for isolation of C-glycosidic alcohols as pure, diastereomeric mixtures. Our methodology was applied to the reduction of aromatic and aliphatic enones which furnished a library of C-glycosidic saturated alcohols from renewable sugars via a green and sustainable approach.