31736-78-4Relevant articles and documents
Lipase-catalyzed synthesis of both enantiomers of 3-chloro-1-arylpropan-1- ols
Pop, Laura Ancua,Czompa, Andrea,Paizs, Csaba,Toa, Monica Ioana,Vass, Elemer,Matyus, Peter,Irimie, Florin-Dan
experimental part, p. 2921 - 2928 (2011/10/13)
The lipase-catalyzed synthesis of both enantiomers of 3-chloro-1-(4- fluorophenyl)propan-1-ol, 3-chloro-1-(4-iodophenyl)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 fluorescens (LAK) followed by the lipase from Candida rugosa (CRL) mediated hydrolysis of previously obtained enantiomerically enriched 1-aryl-3-chloropropyl esters. For the production of enantiopure (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 corresponding (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 chemical calculations. Georg Thieme Verlag Stuttgart - New York.
