title: A highly diastereo- and enantioselective synthesis of tetrahydroquinolines: quaternary stereogenic center inversion and functionalization.
abstract: Tetrahydroquinolines containing two quaternary stereogenic centers were synthesized with excellent ee and dr via a four-component cyclization reaction catalyzed by a chiral phosphoric acid. High chemoselectivity was achieved by differentiating anilines with similar reactivities to yield diverse "hybrid" products. The chirality of the quaternary C4 atom of the 4-aminotetrahydroquinoline products was found to undergo highly stereoselective inversion, enabling facile functionalization using a wide range of nucleophiles (C, O, N, and S).
authors.affiliation: Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School , Shenzhen 518055, China.
authors.forename: Chaosheng
authors.initials: C
authors.lastname: Luo
authors.forename: Yong
authors.initials: Y
authors.lastname: Huang
mesh_terms: D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010756:Phosphoric Acids; D011804:Quinolines; C542964:1,2,3,4-tetrahydroquinoline; C030242:phosphoric acid