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Palladium-Catalyzed γ-Selective and Stereospecific Allyl−Aryl Coupling between Allylic Acetates and Arylboronic Acids

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    Palladium-Catalyzed γ-Selective and Stereospecific Allyl−Aryl Coupling between Allylic Acetates and Arylboronic Acids
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    Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2008, 130, 51, 17276–17277
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    https://doi.org/10.1021/ja808673n
    Published December 3, 2008
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    Abstract

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    Allyl−aryl coupling between allylic acetates and arylboronic acids took place in the presence of catalytic amounts of Pd(OAc)2, 1,10-phenanthroline, and AgSbF6 with high γ-selectivity and E/Z-selectivity. The reaction of an optically active allylic acetates with an α-stereogenic center proceeded with excellent α-to-γ chirality transfer with syn-selectivity and gave the corresponding optically active allyl−aryl coupling products with a stereogenic center at the benzylic position.

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    Cite this: J. Am. Chem. Soc. 2008, 130, 51, 17276–17277
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