Lipase-Catalyzed Desymmetrization of Quaternary Carbon-Containing 1,3 (alpha)-Propanediols: A New TEntry to the Asymmetric Synthesis of Substituted Serine Analogues

A new approach to the asymmetric synthesis of -substituted serine analogues was developed. The method utilizes a lipase-catalyzed esterification desymmetrization protocol. In the presence of PPL, a series of benzyl-substituted quaternary 2nitropropane-1,3-diols were successfully desymmetrized by selective acetylation in very good yields and enantioselectivities (up to 95% ee).