title: Enantioselective Synthesis of Isoquinolines: Merging Chiral-Phosphine and Gold Catalysis.
abstract: The highly enantioselective synthesis of dihydroisoquinoline derivatives from aromatic sulfonated imines tethered with an alkyne moiety, through a one-pot asymmetric relay catalysis of chiral-phosphine and gold catalysts, is reported. Enantiomerically enriched dihydroisoquinoline derivatives were afforded in good yields and good-to-excellent ee values under mild conditions, based on the asymmetric aza-Morita-Baylis-Hillman reaction. Dihydroisoquinoline derivatives containing two chiral centers were also synthesized through further transformations.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, P. R. China.
authors.forename: Yu-Ning
authors.initials: YN
authors.lastname: Gao
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, P. R. China.
authors.forename: Feng-Chen
authors.initials: FC
authors.lastname: Shi
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, P. R. China.
authors.forename: Qin
authors.initials: Q
authors.lastname: Xu
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, P. R. China. mshi@mail.sioc.ac.cn.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China. mshi@mail.sioc.ac.cn.
authors.forename: Min
authors.initials: M
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D006046:Gold / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C109853:G 1617; D007546:Isoquinolines; D010720:Phosphines; D006046:Gold; C044646:phosphine
keywords: Morita-Baylis-Hillman reaction; asymmetric relay catalysis; chiral phosphines; dihydroisoquinoline; gold