title: Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction.
abstract: The direct and catalytic kinetic resolution of racemic carboxylic acids bearing a Brønsted base such as O-protected alpha-hydroxy carboxylic acids and N-protected alpha-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-butyl alcohol for the first time. Highly asymmetric induction [S( k fast/ k slow) = up to 56] has been achieved under the equilibrium between a chiral catalyst and two diastereomeric acylammonium salts through an intramolecular hydrogen-bonding interaction.
authors.affiliation: Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan. ishihara@cc.nagoya-u.ac.jp
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Ishihara
authors.forename: Yuji
authors.initials: Y
authors.lastname: Kosugi
authors.forename: Shuhei
authors.initials: S
authors.lastname: Umemura
authors.forename: Akira
authors.initials: A
authors.lastname: Sakakura