Communication

Origins of Stereoselectivity in Strain-Release Allylations†

  1. Xiyun Zhang Dr.1,
  2. Kendall N. Houk Prof. Dr.1,
  3. James L. Leighton Prof. Dr.2

Article first published online: 28 DEC 2004

DOI: 10.1002/anie.200462130

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 44, Issue 6, pages 938–941, January 28, 2005

Additional Information

How to Cite

Zhang, X., Houk, K. N. and Leighton, J. L. (2005), Origins of Stereoselectivity in Strain-Release Allylations. Angew. Chem. Int. Ed., 44: 938–941. doi: 10.1002/anie.200462130

Author Information

  1. 1

    Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA, Fax: (+1) 310-206-1843

  2. 2

    Department of Chemistry, Columbia University, New York, NY 10027, USA

  1. †

    We are grateful to the National Institute of General Medical Sciences, National Institutes of Health, for financial support of this research.

Publication History

  1. Issue published online: 25 JAN 2005
  2. Article first published online: 28 DEC 2004
  3. Manuscript Received: 27 SEP 2004

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Keywords:

  • allylation;
  • computer chemistry;
  • reaction mechanisms;
  • silanes;
  • stereoselectivity
Thumbnail image of graphical abstract

Explaining the experiment: The transition states for a concerted asymmetric allylation (see scheme) were studied by theoretical methods. The apical attack of the aldehyde oxygen atom on Si accompanied by minimization of electrostatic repulsion in the trigonal-bipyramidal transition state leads to high stereoselectivity.

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