(4RS,5R)- and (4RS,5S)-4-Methoxy-5-methyloxazolidin-2-one Derivatives of Threonine—Interesting Chiral Amidoalkylating Reagents

Authors

  • Dipl.-Chem. Christians Herborn,

    1. Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D-5300 Bonn 1 (FRG)
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  • Andrea Zietlow,

    1. Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D-5300 Bonn 1 (FRG)
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  • Prof. Dr. Eberhard Steckhan

    Corresponding author
    1. Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D-5300 Bonn 1 (FRG)
    • Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D-5300 Bonn 1 (FRG)
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  • This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, BASF AG, and DEGUSSA AG (donation of chemicals). We thank Prof. Dr. E. Breitmaier (Bonn) for carrying out NMR shift and NOE experiments. Communicated in part in lectures delivered at the 20th European Peptide Symposium (Tübingen, September 4–9, 1988) and the 7th EUCHEM Conference on Electrochemistry (Assisi, April 17–22, 1989).

Abstract

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The syntheses of biologically active, complex organic nitrogen-containing compounds often require amidoalkylating reagents. The methoxy groups of the chiral title compounds may be easily substituted by other nucleophiles with good stereochemical control. The key step in this two-step synthesis is the quantitative anodic decarboxylation of the corresponding carboxylic acids (e.g., 12).

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