Preparation of enantiomerically pure α-hydroxymethyl S-tert-butyl sulfones by Candida antarctica lipase catalyzed resolution

Article abstract of DOI:10.1016/0957-4166(96)00135-8

Candida antarctica lipase (CAL; Novozym 435) catalyzed acylation of racemic methyl and benzyl substituted hydroxy sulfones rac-3a and rac-3d, respectively, with vinyl acetate either neat or in ether solvents proceeded with E-values of 18 and 49. For the CAL catalyzed hydrolysis of methyl substituted acetoxy sulfone rac-4a in an emulsion of phosphate buffer and methyl tert-butyl ether at pH 7.0 an E-value of 22 was found. Acetate (+)-ent-4a as well as alcohols (-)-3a and (-)-(S)-3d were obtained with ee-values of 99% on a gram scale.