Iron-Catalyzed Stereospecific Activation of Olefinic C–H Bonds with Grignard Reagent for Synthesis of Substituted Olefins

L Ilies, S Asako, E Nakamura

Index: Ilies, Laurean; Asako, Sobi; Nakamura, Eiichi Journal of the American Chemical Society, 2011 , vol. 133, # 20 p. 7672 - 7675

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Citation Number: 74

Abstract

The reaction of an aryl Grignard reagent with a cyclic or acyclic olefin possessing a directing group such as pyridine or imine results in the stereospecific substitution of the olefinic C–H bond syn to the directing group. The reaction takes place smoothly and without isomerization of the product olefin in the presence of a mild oxidant (1, 2-dichloro-2- methylpropane) and an aromatic cosolvent. Several lines of evidence suggest that the ...