Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part II

Authors

  • Dipl.-Chem. Christian Benkhäuser-Schunk,

    1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-739608
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  • Dipl.-Chem. Boris Wezisla,

    1. Institut für Physikalische und Theoretische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Wegelerstrasse 12, 53115 Bonn (Germany)
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  • Dipl.-Chem. Kirstin Urbahn,

    1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-739608
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  • Dr. Ulf Kiehne,

    1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-739608
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  • Dr. Jörg Daniels,

    1. Institut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
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  • Dr. Gregor Schnakenburg,

    1. Institut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
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  • Prof. Dr. Frank Neese,

    Corresponding author
    1. Max-Planck-Institut für Bioanorganische Chemie, Stiftstrasse 34–36, 45470 Mülheim an der Ruhr (Germany)
    • Max-Planck-Institut für Bioanorganische Chemie, Stiftstrasse 34–36, 45470 Mülheim an der Ruhr (Germany)
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  • Prof. Dr. Arne Lützen

    Corresponding author
    1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-739608
    • Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-739608
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  • Part I: U. Kiehne, T. Bruhn, G. Schnakenburg, R. Fröhlich, G. Bringmann, A. Lützen, Chem. Eur. J. 2008, 14, 4246–4255.

Abstract

Seven racemic derivatives of Tröger’s base—the 1,7-dibromo-substituted derivative 3, the 2,8-dibromo-substituted derivative 4, the 2,8-diiodo-substituted derivative 5, the 3,9-diiodo-substituted derivative 6, the 4,10-dibromo-substituted derivative 7, its singly debrominated analogue 8, and the 2,8-diamino-substituted derivative 9 in its Fmoc-protected form—were synthesized and successfully resolved by (recycling) HPLC on a stationary Whelk-O1 phase at a semipreparative scale. These are valuable functionalized C2-symmetric building blocks for further applications. Their absolute configurations were determined by X-ray crystal structure analysis and/or by comparison of their quantum chemically calculated circular dichroism and UV/Vis spectra with the experimental obtained spectra.

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