Enantioselective Synthesis of α-Substituted Primary Amines by Nucleophilic Addition to Aldehyde-SAMP Hydrazones

Authors

  • Prof. Dr. Dieter Enders,

    Corresponding author
    1. Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
    • Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
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  • Dr. Heinrich Schubert,

    1. Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
    Current affiliation:
    1. Henkel KG, Henkel-Strasse 67, D-4000 Düsseldorf (FRG)
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  • Dipl.-Chem. Christoph Nübling

    1. Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
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  • This work was supported by the Fonds der Chemischen Industrie, by the Minister für Wissenschaft und Forschung des Landes Nordrhein-Westfalen, and by BASF AG, Degussa AG, and Bayer AG. C. N. thanks the Stiftung Volkswagenwerk for a Kekulé Fellowship. We thank Prof. W. A. König, Hamburg, for valuable help with the GC ee-determination.

Abstract

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The optically active primary amines (R)- or (S)-3 having a center of chirality at the α-position can be obtained from the aldehydes 1 via the SAMP hydrazones (S)-2. Addition of R2Li followed by N[BOND]N bond cleavage leads in good yields and enantioselectively (ee = 81–94%) to (R)- or (S)-3.

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