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Branched-Selective Intermolecular Ketone α-Alkylation with Unactivated Alkenes via an Enamide Directing Strategy

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    Branched-Selective Intermolecular Ketone α-Alkylation with Unactivated Alkenes via an Enamide Directing Strategy
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    Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States
    *[email protected]
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2017, 139, 39, 13664–13667
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    https://doi.org/10.1021/jacs.7b08581
    Published September 17, 2017
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    Abstract

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    We describe a strategy for intermolecular branched-selective α-alkylation of ketones using simple alkenes as the alkylating agents. Enamides derived from isoindolin-1-one provide an excellent directing template for catalytic activation of ketone α-positions. High branched selectivity is obtained for both aliphatic and aromatic alkenes using a cationic iridium catalyst. Preliminary mechanistic study favors an Ir–C migratory insertion pathway.

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    Cite this: J. Am. Chem. Soc. 2017, 139, 39, 13664–13667
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