Chemoenzymatic Epoxidation of Alkenes by Dimethyl Carbonate and Hydrogen Peroxide

Abstract

Monoperoxy carbonic acid methyl ester can be generated under neutral conditions by lipase-catalyzed perhydrolysis of dimethyl carbonate with hydrogen peroxide. It can be used in situ for the selective and efficient epoxidation of olefins; the unstable coproduct carbonic acid monomethylester decomposes to carbon dioxide and methanol. Thus, an “acid-free” Prileshajev epoxidation is realized, which is especially useful for the epoxidation of acid-sensitive substrates such as β-pinene.