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Breaking Symmetry with Symmetry: Bifacial Selectivity in the Asymmetric Cycloaddition of Anthracene Derivatives

Authors

  • Dr. Carles Rodríguez-Escrich,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956
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  • Dr. Rebecca L. Davis,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956
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  • Dr. Hao Jiang,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956
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  • Dr. Julian Stiller,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956
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  • Tore K. Johansen,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956
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  • Prof. Dr. Karl Anker Jørgensen

    Corresponding author
    1. Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956
    • Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956
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Abstract

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Push to activate: A new catalytic strategy for the activation of anthracene derivatives has been developed. From symmetrical starting materials, enantioselective cycloaddition reactions can be achieved by employing a C2-symmetric aminocatalyst. This selectivity is due to the gain or loss of conjugation between the enamine and the anthracene in the two transition-state structures. This methodology is demonstrated in 14 examples with 70–96 % yield and 76–95 % ee.

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