LIPASE-CATALYZED ENANTIOSELECTIVE SYNTHESIS OF METHYL (R)-2-TETRADECYLOXIRANECARBOXYLATE AND (S)-2-TETRADECYLOXIRANECARBOXYLATE THROUGH SEQUENTIAL KINETIC RESOLUTION

Among a variety of lipases tested, Pseudomonas fluorescens lipase has been found to induce enantioselective acylation of methyl (R,S)-2-hydr oxy-2-(hydroxymethyl)hexadecanoate (3), affording, through sequential kinetic resolution, both enantiomers in good optical yields. Efficienc y of the process has been compared to the Sharpless asymmetric dihydro xylation of alkene 2 using (DHQD)(2)PHAL and (DHQ)(2)PHAL as chiral li gands. The (R)- and (S)-3 enantiomers have been cyclized to afford bot h enantiomers of methyl 2-tetradecyloxiranecarboxylate (1), a potent h ypoglycemic agent and inhibitor of long-chain fatty acid oxidation.