title: Organocatalytic asymmetric destruction of 1-benzylated Reissert compounds catalysed by quaternary cinchona alkaloids.
abstract: The enantiomeric enrichment of racemic 1-benzylated Reissert compounds under organocatalytic biphasic conditions is presented. The enrichment is the consequence of an asymmetric destruction of the racemic compounds resulting in the formation of the corresponding 1-benzylated isoquinolines. The highest selectivity has been achieved using quaternary cinchona alkaloids as phase-transfer catalysts. The resolution of a number of racemic 1-benzylated Reissert compounds reveals a significant substrate dependence and a proposal for the mechanism of the reaction is presented.
authors.affiliation: Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000, Aarhus C, Denmark.
authors.forename: Kim
authors.initials: K
authors.lastname: Frisch
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D002930:Cinchona Alkaloids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
chemical_list: D002930:Cinchona Alkaloids