title: Evidence of the electronic factor for the highly enantioselective catalytic efficiency of Cinchona-derived phase-transfer catalysts.
abstract: [structure: see text] The Cinchona alkaloid-derived quaternary ammonium salts containing 2'-N-oxypyridine and 2'-cyanobenzene moieties were prepared and evaluated as phase-transfer catalysts in the enantioselective alkylation of glycine imine ester 1. The N-oxypyridine and cyanobenzene moieties might play an important role to form a rigid conformation by coordinating with H(2)O via hydrogen bonding leading to high enantioselectivity (97 approximately >99% ee), which provides evidence of an electronic factor for the high enantioselective catalytic efficiency in phase-transfer alkylation.
authors.affiliation: Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
authors.forename: Mi-Sook
authors.initials: MS
authors.lastname: Yoo
authors.forename: Byeong-Seon
authors.initials: BS
authors.lastname: Jeong
authors.forename: Jeong-Hee
authors.initials: JH
authors.lastname: Lee
authors.forename: Hyeung-Geun
authors.initials: HG
authors.lastname: Park
authors.forename: Sang-Sup
authors.initials: SS
authors.lastname: Jew
mesh_terms: D000478:Alkylation; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D004563:Electrochemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids