title: Preparation of optically active trifluoromethylated (3'-indolyl) thiacarboxylic acids, novel plant growth regulators, through lipase-catalyzed enantioselective hydrolysis.
abstract: Among a variety of lipases tested, that obtained from Candida antarctica (SP 435) induced enantioselective hydrolysis of trifluoroethyl 5,5,5-trifluoro-4-(3'-indolyl)-3-thiapentanoate (1c). The selectivity could be increased by optimizing the reaction conditions. Thus, good selectivity was achieved (E = 37) in a buffer containing 10% dichloroethane. In order to improve the optical yields, a sequential kinetic resolution was utilized for the preparative-scale enantioselective hydrolysis of 1c using SP 435. Hydrolysis of trifluoroethyl 6,6,6-trifluoro-5-(3'-indolyl)-4-thiahexanoate (2c) with the lipase of Pseudomonas aeruginosa (LIP) in a buffer containing 20% tert-amyl alcohol at 25 degrees C gave excellent selectivity (E=357).
authors.affiliation: Department of Chemistry, National Industrial Research Institute of Nagoya, Hirate-cho, Kita-ku, Nagoya 462-8510, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Kato
authors.forename: S
authors.initials: S
authors.lastname: Tanaka
authors.forename: S
authors.initials: S
authors.lastname: Fujii
authors.forename: M
authors.initials: M
authors.lastname: Katayama
authors.forename: H
authors.initials: H
authors.lastname: Kimoto