Insertion of an Alkene into an Ester: Intramolecular Oxyacylation Reaction of Alkenes through Acyl C[BOND]O Bond Activation

Authors

  • Giang T. Hoang,

    1. Department of Chemistry, University of Minnesota, Twin Cities, 207 Pleasant St. SE, Minneapolis, MN 55455 (USA), Fax: (+1) 612-626-7541
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  • Venkata Jaganmohan Reddy,

    1. Department of Chemistry, University of Minnesota, Twin Cities, 207 Pleasant St. SE, Minneapolis, MN 55455 (USA), Fax: (+1) 612-626-7541
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  • Huy H. K. Nguyen,

    1. Department of Chemistry, University of Minnesota, Twin Cities, 207 Pleasant St. SE, Minneapolis, MN 55455 (USA), Fax: (+1) 612-626-7541
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    • UMN Undergraduate Research, 2009–2010.

  • Prof. Christopher J. Douglas

    Corresponding author
    1. Department of Chemistry, University of Minnesota, Twin Cities, 207 Pleasant St. SE, Minneapolis, MN 55455 (USA), Fax: (+1) 612-626-7541
    • Department of Chemistry, University of Minnesota, Twin Cities, 207 Pleasant St. SE, Minneapolis, MN 55455 (USA), Fax: (+1) 612-626-7541
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  • We acknowledge the donors of the ACS Petroleum Research Fund for partial support (47565-G1). We thank UMN (start-up funds), Prof. Gunda Georg for discussions, and Rosalind Douglas for assistance with this manuscript.

Abstract

original image

Atomökonomie und Ester: jetzt kompatibel! Die erste katalytische Insertion einer C[DOUBLE BOND]C-Bindung in eine acylische C-O-Bindung gelang mithilfe von Rhodium-Katalysatoren. Die Produkte sind β-Alkoxyketone mit einem vollständig substituierten Kohlenstoffzentrum. Chelatisierende Chinolingruppen wurden genutzt, um die Rh-Alkoxid-Zwischenstufe zu stabilisieren.

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