title: Remote chirality transfer in nucleophilic catalysis with N-(4-pyridinyl)-L-proline derivatives.
abstract: Chiral nucleophilic catalysts 5-15 were prepared starting from L-proline. Catalysts 9 and 14 promoted acylative kinetic resolution of racemic amino alcohol derivative 16 with selectivity factors of 8.1 and 11, respectively, at ambient temperature. Since chiral elements are not present in the catalytically active pyridine ring in these catalysts, chirality transfer from the remote stereogenic center to the reactive site (N-acylpyridinium) is suggested to be responsible for the differentiation between enantiomers.
authors.affiliation: Institute for Chemical Research, Kyoto University, Uji, Kyoto, Japan. kawabata@scl.kyoto-u.ac.jp
authors.forename: Takeo
authors.initials: T
authors.lastname: Kawabata
authors.forename: Roland
authors.initials: R
authors.lastname: Stragies
authors.forename: Takayuki
authors.initials: T
authors.lastname: Fukaya
authors.forename: Kaoru
authors.initials: K
authors.lastname: Fuji
mesh_terms: D000215:Acylation; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011725:Pyridines; D011392:Proline