Green Organocatalytic Dihydroxylation of Alkenes

A cheap, green and metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 was employed as the oxidant and 2,2,2-trifluoroacetophenone as the organocatalyst, leading to a highly sustainable protocol, where a variety of homoallylic alcohols, amino-alkenes and double bonds were converted into the corresponding polyalcohols in high to excellent yields. This manifold takes advantage of an epoxidation reaction, followed by an in situ acidic treatment of the reaction mixture, upon which water ring opens the three-membered ring, leading to the desired products.