Organocatalytic asymmetric destruction of 1-benzylated Reissert compounds catalysed by quaternary cinchona alkaloids.
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.
Frisch
Kim
K
Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000, Aarhus C, Denmark.
Jørgensen
Karl Anker
KA
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D002930:Cinchona Alkaloids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D002930:Cinchona Alkaloids