A Template Synthesis of Stable Conjugated Primary Enamines from Ketones, Nitriles, and Butadiene

Authors

  • Dr. Luis López,

    1. Organisch-chemisches Institut der Universität, Correnstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-977
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  • Dipl.-Chem. Martin Berlekamp,

    1. Organisch-chemisches Institut der Universität, Correnstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-977
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  • Dipl.-Chem. Dorothee Kowalski,

    1. Organisch-chemisches Institut der Universität, Correnstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-977
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  • Prof. Dr. Gerhard Erker

    Corresponding author
    1. Organisch-chemisches Institut der Universität, Correnstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-977
    • Organisch-chemisches Institut der Universität, Correnstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-977
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  • This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and the Alfried Krupp von Bohlen and Halbach Foundation. Dr. L. López thanks the Ministerio de Educacion y Ciencia, Madrid, and the Alexander von Humboldt Foundation for research grants. We thank Prof. Dr. W. R. Roth for interesting discussions and suggestions.

Abstract

original image

The energy of conjugation of butadiene is sufficient to favor the primary enamines 3 over the imine tautomers 2 under equilibrium conditions. They are now readily accessible by template synthesis via the imine intermediates 1. R1 = Ph, -CH2CH2-, CH3; R2 - Ph, tBu, p-CH3C6H4, p-NCC6H4, CH[DOUBLE BOND]CHCN.

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