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

Abstract

Abstract Candida antarctica lipase (CAL; Novozym 435) catalyzed acylation of racemic methyl and benzyl substituted hydroxy sulfones rac- 3 a , 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- 4 a in an emulsion of phosphate buffer and methyl tert -butyl ether at pH 7.0 an E -value of 22 was found. Acetate (+)-ent- 4 a as well as alcohols (−)- 3a and (−)-(S)- 3 d were obtained with ee-values of 99% on a gram scale.