Chemo-enzymatic synthesis of (R)- and (S)-3,4-dichlorophenylbutanolide intermediate in the synthesis of sertraline

3,4-Dichlorophenacylchloride was reduced with whole cell biocatalysts to give the (R)- or (S)-chrorohydrine in high yields and good to high enantiomeric excess. Yields and enantiomeric purity of the (S)-enantiomer were increased to 95 and >98%, respectively, using growing cells from Geotrichum candidum (CBS 233.76) in the presence of hydrophobic adsorbing resins at 4 g/l. The latter compound was transformed into (R)-3,4-dichlorophenylbutanolide, intermediate in the synthesis of (+)-cis-1S,4S-sertraline. (C) 1999 Elsevier Science Ltd. All rights reserved.