A general procedure for the asymmetric synthesis of 3-aryl-1,2,3,4-tetrahydroisoquinolines |
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| Affiliation: | 1. Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, Austria;2. Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St, Cambridge, MA 02138, USA;3. Medicines Research Centre, GlaxoSmithKline, Gunnel''s Wood Road, Stevenage, Herts SG1 2NY, United Kingdom;1. Department of Chemistry, University of Houston, College of Natural Sciences and Mathematics, Houston, TX 77204, United States;2. Department of Pharmacological and Pharmaceutical Sciences, University of Houston, College of Pharmacy, Houston, TX 77204, United States;1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran;2. F H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan;1. Catalytic Processes and Materials, MESA+ Institute for Nanotechnology, University of Twente, Enschede 7500AE, The Netherlands;2. Aalto University, School of Chemical Technology, Department of Biotechnology and Chemical Technology, P.O. Box 16100, 00076 Aalto, Finland;1. Department of Organic Chemistry, Institute of Chemical Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic;2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences, 16610 Prague 6, Czech Republic |
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| Abstract: | A general procedure for the asymmetric synthesis of 3-aryl-1,2,3,4-tetrahydroisoquinolines with any desired substitution pattern at both aromatic rings is reported. The methodology relies on the deoxygenation of 3-aryl-1,2,3,4-tetrahydroisoquinolin-4-ols 1a–e, which can be easily prepared from chiral non-racemic arylglycines under ionic hydrogenation conditions The target heterocycles are obtained as almost enantiomerically pure compounds. Further experiments allow establishing that this transformation occurs via SN1 mechanism in which a carbocationic intermediate species is firstly formed and afterwards it undergoes rapid reaction with a nucleophilic hydride carrier to afford the reduction product. |
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