L. Pop, A. Czompa, Csaba Paizs
Sep 1, 2011
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Journal
Synthesis
Abstract
The lipase-catalyzed synthesis of both enantiomers of 3- chloro-1-(4-fluorophenyl)propan-1-ol, 3-chloro-1-(4-iodophe- nyl)propan-1-ol, and 3-chloro-1-phenylpropan-1-ol is described. The procedure is based on the enantiomer-selective acylation of the racemic alcohols in presence of lipase from Pseudomonas fluore- scens (LAK) followed by the lipase from Candida rugosa (CRL) mediated hydrolysis of previously obtained enantiomerically en- riched 1-aryl-3-chloropropyl esters. For the production of enan- tiopure (S)-1-aryl-3-chloropropan-1-ols (99% ee, 34-42% yield) the reactions were stopped at higher conversions than the theoretical optimum of 50%, while for enantiopure (R)-1-aryl-3-chloropropyl acetates (99% ee) the reactions were stopped at lower conversions. The latter compounds were enzymatically hydrolyzed into the cor- responding (R)-1-aryl-3-chloropropan-1-ols (97-99% ee, 18-24% yield). The absolute configuration of the resolution products was determined by VCD measurements combined with quantum chem- ical calculations.