Efficient epoxidation of alkenes with hydrogen peroxide, lactone, and lipase

Abstract

A green and efficient oxidation system containing hydrogen peroxide, lactone, and lipase was developed for the epoxidation of alkenes. A variety of alkenes was oxidized with this system, giving 87-95% analytical yield of the corresponding epoxides. The epoxidation occurred via lipase-catalyzed formation of hydroxy peroxy acid from lactone, without release of any harmful short-chain acid and alcohol, and in situ chemical oxidation of alkenes. Both hydrophilic ε-caprolactone and hydrophobic δ-decanolactone were shown to be good substrates to produce hydroxy peracids and good reaction solvents, and the method is suitable for the oxidation in either single phase or two-liquid phase. In comparison with other lipase-mediated oxidation systems, the new oxidation system gave higher yield, higher efficiency, and higher enzyme stability. © 2009 The Royal Society of Chemistry.