Gold-Catalyzed Intramolecular Allylic Amination of 2-Tosylaminophenylprop-1-en-3-ols. A Concise Synthesis of (±)-Angustureine

Prasath Kothandaraman, Shi Jia Foo and Philip Wai Hong Chan*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: waihongntu.edu.sg

P. Kothandaraman, S. J. Foo, P. W. H. Chan, J. Org. Chem., 2009, 74, 5947-5952.

DOI: 10.1021/jo900917q

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Abstract

An efficient synthetic route to 1,2-dihydroquinolines relies on AuCl₃/AgSbF₆-catalyzed intramolecular allylic amination of 2-tosylaminophenylprop-1-en-3-ols in good yields. The method was shown to be applicable to a broad range of 2-tosylaminophenylprop-1-en-3-ols containing electron-withdrawing, electron-donating, and sterically demanding substrate combinations.

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Key Words

1,2-dihydroquinolines

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ID: J42-Y2009-2470