Lipase-Catalyzed Enantioselective Synthesis of Methyl (R)- 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-hydroxy-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) 2 PHAL and (DHQ) 2 PHAL as chiral ligands. The ( R )- and ( S )- 3 enantiomers have been cyclized to afford both enantiomers of methyl 2-tetradecyloxiranecarboxylate ( 1 ), a potent hypoglycemic agent and inhibitor of long-chain fatty acid oxidation.