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Titanium-Induced Zipper Reactions

Authors

  • Priv.-Doz. Dr. Alois Fürstner,

    Corresponding author
    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr (FRG) Telefax: Int. code + (208)306 2980
    • Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr (FRG) Telefax: Int. code + (208)306 2980
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  • Dipl.-Chem. Arne Ptock,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr (FRG) Telefax: Int. code + (208)306 2980
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  • Holger Weintritt,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr (FRG) Telefax: Int. code + (208)306 2980
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  • Dr. Richard Goddard,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr (FRG) Telefax: Int. code + (208)306 2980
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  • Prof. Dr. Carl Krüger

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr (FRG) Telefax: Int. code + (208)306 2980
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  • This work was supported by the Volkswagen Stiftung and the Fonds der Chemischen Industrie.

Abstract

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Remarkably high chemo- and regioselectivity was found in the intramolecular one-pot McMurray-type reaction between ketone and amide carbonyl groups. A simple preparative method is used by which the active low-valent titanium species is formed selectively at the site of the reductive coupling. For example, compound 2 is formed from 1 in 86% yield by a zipper-like series of carbonyl couplings.

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