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Michael Addition of N-Unprotected 2-Oxindoles to Nitrostyrene Catalyzed by Bifunctional Tertiary Amines: Crucial Role of Dispersion Interactions

Authors

  • Christoph Reiter,

    1. Chair of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nuremberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-85-22865
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    • These authors contributed equally to this work.

  • Sònia López-Molina,

    1. Chair of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nuremberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-85-22865
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    • These authors contributed equally to this work.

  • Bernhard Schmid,

    1. Chair of Theoretical Chemistry and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander University of Erlangen-Nuremberg, Egerlandstraße 3, 91058 Erlangen (Germany), Fax: (+49) 9131-85-27736
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  • Dr. Christian Neiss,

    1. Chair of Theoretical Chemistry and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander University of Erlangen-Nuremberg, Egerlandstraße 3, 91058 Erlangen (Germany), Fax: (+49) 9131-85-27736
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  • Prof. Dr. Andreas Görling,

    Corresponding author
    1. Chair of Theoretical Chemistry and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander University of Erlangen-Nuremberg, Egerlandstraße 3, 91058 Erlangen (Germany), Fax: (+49) 9131-85-27736
    • Andreas Görling, Chair of Theoretical Chemistry and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander University of Erlangen-Nuremberg, Egerlandstraße 3, 91058 Erlangen (Germany), Fax: (+49) 9131-85-27736===

      Svetlana B. Tsogoeva, Chair of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nuremberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-85-22865===

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  • Prof. Dr. Svetlana B. Tsogoeva

    Corresponding author
    1. Chair of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nuremberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-85-22865
    • Andreas Görling, Chair of Theoretical Chemistry and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander University of Erlangen-Nuremberg, Egerlandstraße 3, 91058 Erlangen (Germany), Fax: (+49) 9131-85-27736===

      Svetlana B. Tsogoeva, Chair of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nuremberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-85-22865===

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Abstract

Bifunctional thiourea- or sulfonamide-derived tertiary amines catalyze the enantioselective nitro-Michael addition of N-unprotected 3-substituted 2-oxindoles to nitrostyrene in up to 99 % yields, 94:6 er, and 87:13 dr. Overcoming the necessity to introduce and remove activating or protecting groups at the nitrogen moiety leads to a reduction of energy use, costs, and waste. Transition-state geometries for the formation of all possible stereoisomers in the nitro-Michael addition of N-unprotected 3-substituted 2-oxindole to nitrostyrene catalyzed by Takemoto’s tertiary amine–thiourea are calculated. It is shown that the relative positions and binding patterns of the reactants and the catalyst molecule are largely determined by van der Waals interactions.

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