Epoxidation Of Allylic Alcohols In Aqueous Solutions Of Simple Sugars

It may be surpising to find that aqueous solutions of simple sugars such as sucrose, L-arabinose or methyl ß-D-fructopyranose contain some hydrophobic regions. Thus organic compounds have enhanced solubility in water in the presence of these sugars. Epoxidation of allylic alcohols takes place in such solutions with hydrogen peroxide and molybdic or tungstic salts as catalysts. No oxidation of the alcohol or ring opening of the epoxide takes place, rates are often enhanced, and the erythro to threo ratio of certain alcohols is increased, when compared to mCPBA oxidations. Arabinose gives the best results with Mo catalysts (Denis C et al, Chem Commun, 2001, 2460).