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Synlett 1991; 1991(10): 721-723
DOI: 10.1055/s-1991-34777
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A Mild and Convenient High-Yield Alternative to the Protic Acid Catalysed Pictet-Spengler Synthesis of Tetrahydroisoquinolines

Gi K. Cheung* , Martyn J. Earle, Robin A. Fairhurst, Harry Heaney, Khamis F. Shuhaibar, Stephen C. Eyley, Francis Ince
  • *Department of Chemistry, Loughborough University of Technology, Leicestershire, LE11 3TU, England
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Publication Date:
13 March 2002 (online)

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The preparation of N-alkoxycarbonyl-N-(1-methoxyalkyl)-2-arylethylamine derivatives 3 and their cyclisation to 1-substituted 1,2,3, 4-tetrahydroisoquinoline derivatives 4 in high yields is described using trimethylsilyl trifluoromethanesulphonate, titanium(IV) chloride or, in the case of activated 2-arylethylamine derivatives, chlorotrimethylsilane.