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A Practical Strategy for the Structural Diversification of Aliphatic Scaffolds through the Palladium-Catalyzed Picolinamide-Directed Remote Functionalization of Unactivated C(sp3)[BOND]H Bonds

Authors

  • Dr. Gang He,

    1. Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA), Fax: (+1) 814-863-5319
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  • Prof. Dr. Gong Chen

    Corresponding author
    1. Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA), Fax: (+1) 814-863-5319
    • Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA), Fax: (+1) 814-863-5319
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  • We thank the Pennsylvania State University for support of this research.

Abstract

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Hats off to the director: High levels of regio- and stereoselectivity were observed for a broad range of amine substrates with aryl and vinyl iodide coupling partners in the title reaction. The synthetic utility of this strategy was highlighted by the ready preparation from threonine of 1, with a removable picolinamide auxiliary PAr, and its coupling with 2 in a concise formal synthesis of (+)-obafluorin. TBS=tert-butyldimethylsilyl.

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