Origins of Stereoselectivity in Strain-Release Allylations


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


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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.