PREPARATION OF ENANTIOMERICALLY PURE ALPHA-HYDROXYMETHYL S-TERT-BUTYLSULFONES BY CANDIDA-ANTARCTICA LIPASE-CATALYZED RESOLUTION

Candida antarctica lipase (CAL; Novozym 435) catalyzed acylation of ra cemic methyl and benzyl substituted hydroxy sulfones rac-3a and rac-3d , respectively, with vinyl acetate either neat or in ether solvents pr oceeded with E-values of 18 and 49. For the CAI, catalyzed hydrolysis of methyl substituted acetoxy sulfone rac-4a in an emulsion of phospha te buffer and methyl tert-butyl ether at pH 7.0 an E-value of 22 was f ound. Acetate (+)-emt-4a as well as alcohols (-)-3a and (-)-(S)-3d wer e obtained with ee-values of 99% on a gram scale. Copyright (C) 1996 E lsevier Science Ltd