Enantioselective transesterification of racemic phenyl ethanol and its derivatives in organic solvent and ionic liquid using Pseudomonas aeruginosa lipase

The transesterification of 1-phenyl ethanol has been carried Out using lipases from Pseudomonas aeruginosa MTCC 5113, to obtain chirally pure aryl ethanols with good yield and excellent enantioselectivity. The lipase from A aeruginosa gave good conversion and moderate enantioselectivity (ee) in organic solvents, however, when the catalytic amount of ionic liquids were added in the reaction mixture, excellent enantioselectivity was obtained. Moreover, the change in enantiomer preference was seen in the presence of catalytic amount of ionic liquids. The findings revealed that hydrophobic ionic liquids (two-phase system) were the best solvents and 4-substituted aryl ethanols were the pre-eminent Substrates for such type of reactions. The preparative scale (5 g) transesterification of 1-phenylethanol using lipases from P. aeruginosa yielded S-(-)-1-phenyl ethanol with 39% yield and >99% ee in hexane and 46% yield and >99% ee in [BMIm][PF6]. (C) 2009 Elsevier Ltd. All rights reserved.