We are grateful to the National Institute of General Medical Sciences, National Institutes of Health, for financial support of this research.
Origins of Stereoselectivity in Strain-Release Allylations†
Article first published online: 28 DEC 2004
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 44, Issue 6, pages 938–941, January 28, 2005
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
- Issue published online: 25 JAN 2005
- Article first published online: 28 DEC 2004
- Manuscript Received: 27 SEP 2004
- computer chemistry;
- reaction mechanisms;
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.