Residual Dipolar Couplings as a Powerful Tool for Constitutional Analysis: The Unexpected Formation of Tricyclic Compounds

Authors

  • Dr. Grit Kummerlöwe,

    1. Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany)
    2. Current address: Institut für Biologische Grenzflächen (IBG-2), Karlsruher Institut für Technologie, Postfach 3640, 76021 Karlsruhe (Germany)
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  • Dr. Benedikt Crone,

    1. Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany)
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  • Manuel Kretschmer,

    1. Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany)
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  • Prof. Dr. Stefan F. Kirsch,

    Corresponding author
    1. Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany)
    • Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany)
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  • Prof. Dr. Burkhard Luy

    Corresponding author
    1. Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany)
    2. Current address: Institut für Organische Chemie, Karlsruher Institut für Technologie, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany)
    • Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany)
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  • S.F.K. thanks the Deutsche Forschungsgemeinschaft (DFG) and the Fonds der Chemischen Industrie (FCI) for support. B.L. thanks the FCI and the DFG (Heisenberg program LU 835/2,3,4,7 and Forschergruppe FOR 934).

Abstract

original image

Analyze this! Residual dipolar couplings (RDCs) can be used to determine the constitution of a small molecule when traditional methods for structure elucidation fail. In a case study, a highly congested, tricyclic compound resulting from the electrophilic cyclization of an azide-containing 1,5-enyne was investigated.

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