title: Organocatalytic enantioselective Pictet-Spengler reactions for the syntheses of 1-substituted 1,2,3,4-tetrahydroisoquinolines.
abstract: A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam , Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Elma
authors.initials: E
authors.lastname: Mons
authors.forename: Martin J
authors.initials: MJ
authors.lastname: Wanner
authors.forename: Steen
authors.initials: S
authors.lastname: Ingemann
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005021:Ethylamines / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis / Q000737:chemistry; D009578:Nitrobenzenes / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018091:Receptors, AMPA / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000081:Acetamides; C406944:BINOL, naphthol; D001688:Biological Products; D005021:Ethylamines; D007546:Isoquinolines; D009284:Naphthols; D009578:Nitrobenzenes; D009943:Organophosphorus Compounds; D018091:Receptors, AMPA; D044005:Tetrahydroisoquinolines; C523713:crispine A; C519150:almorexant