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A Highly Enantioselective Overman Rearrangement through Asymmetric Counteranion-Directed Palladium Catalysis

Authors

  • Dr. Gaoxi Jiang,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
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    • These authors contributed equally to this work.

  • Dr. Rajkumar Halder,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
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    • These authors contributed equally to this work.

  • Dr. Yewen Fang,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
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    • These authors contributed equally to this work.

  • Prof. Dr. Benjamin List

    Corresponding author
    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
    • Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
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  • Generous support by the Max Planck Society is acknowledged. We also thank our HPLC and GC departments for their support.

Abstract

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The chiral TRIP anion combined with a simple commercially available palladacycle furnishes a highly active catalyst for the enantioselective rearrangement of allylic imidates to the corresponding amide products in high yields (see scheme). The stereoselectivity is induced entirely by the chiral phosphate anion although the catalyst complex contains a chiral palladacycle (see scheme).

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