SOLVENT EFFECTS IN LIPASE-CATALYZED TRANSESTERIFICATION REACTIONS

Porcine pancreatic lipase-catalysed transesterifications of 2,2,2-trifluoroethyl butyrate with racemic 2-octanol and 1-phenylethanol have been studied in different organic solvents. Solvent hydrophobicity (log P -1.1 to 3.3) has only a minor effect on the reaction rate. Independently of the solvent used as the reaction medium, both (R)-2-octyl and (R)-1-phenylethyl butyrates were obtained in high optical purity (ee greater than 90%). Candida cylindracea lipase is active only in the most hydrophobic solvents studied.