title: The synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor.
abstract: Optically active atropisomeric N-(2,5-di-tert-butylphenyl)-1,2,3,4-tetrahydroquinoline with an N-C chiral axis was prepared via a catalytic enantioselective reaction. The addition of methane sulfonic acid to this axially chiral quinoline dramatically lowered the barrier to rotation around the chiral axis.
authors.affiliation: Department of Applied Chemistry, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo, 135-8458, Japan. kitagawa@shibaura-it.ac.jp.
authors.forename: Yuya
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Masato
authors.initials: M
authors.lastname: Kageyama
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Morisawa
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Dobashi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Hasegawa
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yokojima
authors.forename: Osamu
authors.initials: O
authors.lastname: Kitagawa
mesh_terms: D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000143:Acids; D011804:Quinolines; C542964:1,2,3,4-tetrahydroquinoline