Lipase-catalyzed enantioselective synthesis of methyl (R)- and (S)-2-tetradecyloxiranecarboxylate through sequential kinetic resolution

摘要

Among a variety of lipases tested, pseudomonas fluorescens lipase have been found to induced enatioselective acylation of methyl (R,S)-2-hydoxy-2-(hydroxymethyl)hexadecanoate (3), affording, through sequential kinetic resolution, both enantiomers in good optical yields. Efficiency of the process has been compared to the Sharpless asymmetric dihydroxylation of alkene 2 using (DHQD)_2PHAL and (DHQ)_2PHAL as chiral ligands.