The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols

The enantioselectivity of the lipase from Pseudomonas cepacia (PCL) in the transesterification of 2-phenyl-1-propanol I was studied using a series of vinyl 3-arylpropanoates as acyl donors. The most enantioselective transeste rification reaction of the alcohol was attained by using vinyl 3-(p-iodophe nyl)- or 3-(p-trifluoromethylphenyl)propanoates, with enantiomer ratios, E, of 116 and 138, respectively. Vinyl 3-phenylpropanoate was also effective for the resolution of 1 mediated by lipases from P. fluorescens and porcine pancreas and for the PCL-catalysed transesterification of several 2-phenyl -1-alkanols. The enantiomeric resolution of 1 was practically carried out b y the first enantioselective transesterification using PCL and vinyl 3-(p-i odophenyl)propanoate to afford (R)-1 and then the enantioselective hydrolys is of the resultant ester to afford (S)-1. (C) 2001 Elsevier Science Ltd. A ll rights reserved.