title: Kinetic resolution of racemic alpha-arylalkanoic acids with achiral alcohols via the asymmetric esterification using carboxylic anhydrides and acyl-transfer catalysts.
abstract: A variety of optically active carboxylic esters are produced by the kinetic resolution of racemic alpha-substituted carboxylic acids using achiral alcohols, aromatic or aliphatic carboxylic anhydrides, and chiral acyl-transfer catalysts. The combination of 4-methoxybenzoic anhydride (PMBA) or pivalic anhydride with the modified benzotetramisole-type catalyst ((S)-beta-Np-BTM) is the most effective for promotion of the enantioselective coupling reaction between racemic carboxylic acids and a novel nucleophile, bis(alpha-naphthyl)methanol, to give the corresponding esters with high ee's. This protocol was successfully applied to the production of nonracemic nonsteroidal anti-inflammatory drugs from racemic compounds utilizing the transacylation process to generate the mixed anhydrides from the acid components with the suitable carboxylic anhydrides.
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@rs.kagu.tus.ac.jp
authors.forename: Isamu
authors.initials: I
authors.lastname: Shiina
authors.forename: Kenya
authors.initials: K
authors.lastname: Nakata
authors.forename: Keisuke
authors.initials: K
authors.lastname: Ono
authors.forename: Yu-suke
authors.initials: YS
authors.lastname: Onda
authors.forename: Makoto
authors.initials: M
authors.lastname: Itagaki
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism; D013773:Tetramisole / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000438:Alcohols; D000812:Anhydrides; D002264:Carboxylic Acids; D004952:Esters; C515434:benzotetramisole; D013773:Tetramisole