title: Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines.
abstract: A chiral Brønsted acid catalyzed dehydrogenative kinetic resolution of tetrahydroquinoline derivatives, which are representative of cyclic secondary amines, based on their hydrogen transfer to aromatic imines was efficiently achieved with high enantioselectivities. This hydrogen transfer of tetrahydroquinolines to imines was not driven by their aromatization to quinolines. This dehydrogenative kinetic resolution could be also applied to the asymmetric synthesis of various benzofused heterocycles containing secondary amine cores.
authors.affiliation: Department Chemistry, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan. takahiko.akiyama@gakushuin.ac.jp.
authors.forename: Kodai
authors.initials: K
authors.lastname: Saito
authors.forename: Hiromitsu
authors.initials: H
authors.lastname: Miyashita
authors.forename: Takahiko
authors.initials: T
authors.lastname: Akiyama
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010756:Phosphoric Acids / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
chemical_list: D000588:Amines; D007097:Imines; D010756:Phosphoric Acids; D011804:Quinolines; D006859:Hydrogen; C542964:1,2,3,4-tetrahydroquinoline; C030242:phosphoric acid