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Active Conformation in Amine–Thiourea Bifunctional Organocatalysis Preformed by Catalyst Aggregation

Authors

  • Dr. Gábor Tárkányi,

    Corresponding author
    1. Department of NMR Spectroscopy, Institute of Structural Chemistry, Hungarian Academy of Sciences, Pusztaszeri út 59-67, Budapest, 1025 (Hungary), Fax: (+36) 1-438-1107
    • Department of NMR Spectroscopy, Institute of Structural Chemistry, Hungarian Academy of Sciences, Pusztaszeri út 59-67, Budapest, 1025 (Hungary), Fax: (+36) 1-438-1107
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  • Dr. Péter Király,

    1. Department of NMR Spectroscopy, Institute of Structural Chemistry, Hungarian Academy of Sciences, Pusztaszeri út 59-67, Budapest, 1025 (Hungary), Fax: (+36) 1-438-1107
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  • Dr. Tibor Soós,

    1. Department of Synthetic Organic Chemistry, Institute of Biomolecular Chemistry, Hungarian Academy of Sciences, Pusztaszeri út 59-67, Budapest, 1025 (Hungary)
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  • Szilárd Varga

    1. Department of Synthetic Organic Chemistry, Institute of Biomolecular Chemistry, Hungarian Academy of Sciences, Pusztaszeri út 59-67, Budapest, 1025 (Hungary)
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Abstract

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Self-activation: Takemoto's catalyst gains access to its active conformation by equilibrating between its hydrogen-bonded intra- and intermolecular interactions in apolar aprotic solvents. By destabilization of the inactive monomeric conformations, the extended antianti thiourea conformation is preformed in the assembly. On leaving the assembly, this transient conformation has a structural preference to become a catalytically active monomeric species that has the potency for dual activation (see scheme).

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