title: Enantioselective BINOL-phosphoric acid catalyzed Pictet-Spengler reactions of N-benzyltryptamine.
abstract: Optically active tetrahydro-beta-carbolines were synthesized via an ( R)-BINOL-phosphoric acid-catalyzed asymmetric Pictet-Spengler reaction of N-benzyltryptamine with a series of aromatic and aliphatic aldehydes. The tetrahydro-beta-carbolines were obtained in yields ranging from 77% to 97% and with ee values up to 87%. The triphenylsilyl-substituted BINOL-phosphoric acid proved to be the catalyst of choice for the reaction with aromatic aldehydes. For the aliphatic aldehydes, 3,5-bistrifluoromethylphenyl-substituted BINOL-phosphoric acid was identified as the best catalyst.
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.
authors.forename: Nishant V
authors.initials: NV
authors.lastname: Sewgobind
authors.forename: Martin J
authors.initials: MJ
authors.lastname: Wanner
authors.forename: Steen
authors.initials: S
authors.lastname: Ingemann
authors.forename: René
authors.initials: R
authors.lastname: de Gelder
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D009284:Naphthols / Q000737:chemistry*; D010084:Oxidation-Reduction; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000447:Aldehydes; C406944:BINOL, naphthol; D001593:Benzyl Compounds; D002243:Carbolines; D009284:Naphthols; D010756:Phosphoric Acids; D014363:Tryptamines