Microbial desymmetrization of 3-arylglutaronitriles, an unusual enhancement of enantioselectivity in the presence of additives

In the presence of an organic additive such as acetone or beta -cyclodextri n or in a biphasic system of hexane and aqueous phosphate buffer, microbial desymmetrization of 3-arylglutaronitriles catalyzed by Rhodococcus sp. AJ2 70 cells proceeded regiospecifically and enantioselectively to produce S-()-3-aryl-4-cyanobutyric acids in high enantiomeric excess. Convenient chemo enzymatic syntheses of optically active R-(-)-4-amino-3-phenylbutyric acid and 4R-(-)-4-phenyltetrahydropyran-2-one are described. (C) 2000 Elsevier S cience Ltd. All rights reserved.