Communication

Diastereoselective Benzylic Arylation of Tetralins

  1. Marion Davoust Dr.1,
  2. Jacki A. Kitching Dr.1,
  3. Matthew J. Fleming Dr.2,
  4. Mark Lautens Prof. Dr.1

Article first published online: 24 NOV 2009

DOI: 10.1002/chem.200902694

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 16, Issue 1, pages 50–54, January 4, 2010

Additional Information

How to Cite

Davoust, M., Kitching, J., Fleming, M. and Lautens, M. (2010), Diastereoselective Benzylic Arylation of Tetralins. Chemistry - A European Journal, 16: 50–54. doi: 10.1002/chem.200902694

Author Information

  1. 1

    Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S3H6 (Canada), Fax: (+1) 416-946-8185

  2. 2

    Chemical Development and Catalysis Department, Solvias AG, WRO-1055.6.62, P.O. Box, 4002 Basel (Switzerland)

Publication History

  1. Issue published online: 23 DEC 2009
  2. Article first published online: 24 NOV 2009
  3. Manuscript Received: 30 SEP 2009

Funded by

  • Natural Sciences and Engineering Research Council of Canada
  • NSERC
  • French ‘Ministère des Affaires Etrangères’ (Bourse Lavoisier)

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Keywords:

  • alkylation;
  • benzylic alcohols;
  • carbocations;
  • diastereoselectivity;
  • electrophilic aromatic substitution

Graphical Abstract

Thumbnail image of graphical abstract

Friedel–Crafts protocols for the intermolecular, trans-selective benzylic arylation of tetralin systems are described (see scheme). The protocols have broad substrate scope and the use of enantiopure substrates allows the preparation of trans-aryl-substituted tetralins in high ee.

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