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Unexpected Formation of 3-Substituted 1,2,3,4-Tetrahydroisoquinolines during Tosylation of N,N-dibenzylaminols

S. Chandrasekhar, Pradyumna K. Mohanty, K. Harikishan and Pradip K. Sasmal

*Division of Natural Products Chemistry, CSIR - Indian Institute of Chemical Technology, Hyderabad, 500007, India, Email:

S. Chandrasekhar, P. K. Mohanty, K. Harikishan, P. K. Sasmal, Org. Lett., 1999, 1, 877-879.

DOI: 10.1021/ol9901220


An intramolecular Friedel-Crafts cyclization of an in situ generated tosylate intermediate enables an efficient construction of 3-substituted 1,2,3,4-tetrahydroisoquinolines from N,N-dibenzyl-α-aminols.

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Key Words

tetrahydroisoquinolines, Friedel-Crafts alkylation

ID: J54-Y1999