Optical resolution of racemic alcohols

摘要

Optical resolution of racemic alcohols of formula (I) comprises reacting (I) with a vinyl, propenyl or isopropenyl ester (II) of a 2-10C alkane- or alkene-di- or tricarboxylic acid in the presence of a lipase, isolating the unconverted enantiomer, and opt. recovering the other enantiomer from the resulting ester: B-A-(OH)C(H)-R1 (I); R1 = COOH, 2-5C alkoxycarbonyl, CN, or 1-4C alkyl which is opt. unsatd. and opt. substd. by halo, 1-4C alkoxy, methylenedioxy, ethylenedioxy, NH2, 1-4C alkylamino, NHSO2Me, COMe, COOH, 2-5C alkoxycarbonyl, NO2, CN and/or N3; A = a single bond, 1-4C alkylene or 2-6C alkenylene; B = phenyl, naphthyl, pyridyl, pyrimidyl, furyl, thienyl or imidazolyl; 1-20C alkyl, opt. contg. one or more double or triple bonds and opt. with one or more CH2 gps. replaced by CO, O, NH or 1-4C alkylimino; or opt. unsatd. 3-7C cycloalkyl, opt. with a CH2 gp. replaced by CO and opt. with 1-2 CH2 gps. replaced by O or NH; where B is opt. substd. by halo, 1-4C alkoxy, methylenedioxy, ethylenedioxy, NH2, 1-4C alkylamino, NHSO2Me, COMe, COOH, 2-5C alkoxycarbonyl, NO2, CN and/or N3; or when A is a single bond, R1+B = a 3-8C alkylene or alkenylene gp. in which 2 CH2 gps. are opt. bridged by a 1-4C alkylene gp. and one or more CH2 gps. are opt. replaced by CO, O, NH or 1-4C alkylimino, the resulting ring being opt. substd. by 1-4C alkoxy, methylenedioxy, ethylenedioxy, NH2, 1-4C alkylamino, NHSO2Me, COMe, COOH, 2-5C alkoxycarbonyl, NO2, CN and/or N3.