Electroauxiliary-Assisted Sequential Introduction of Organic Groups on the α-Carbons of Nitrogen

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  • SUGA Seiji
    Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University
  • WATANABE Mitsuru
    Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University
  • SONG Chun-Hong
    Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University
  • YOSHIDA Jun-ichi
    Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University

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Other Title
  • Electroauxiliary Assisted Sequential Introduction of Organic Groups on the アルファ Carbons of Nitrogen
  • Electroauxiliary-Assisted Sequential Introduction of Organic Groups on the .ALPHA.-Carbons of Nitrogen

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Abstract

A method for sequential introduction of two organic groups on the same or the different α-carbons of nitrogen has been developed based on a combination of the concept of electroauxiliary and the cation pool method. Selective introduction of two carbon nucleophiles into 2,5- or 2,2-position of pyrrolidine has been accomplished via sequential electrochemical oxidation of pyrrolidine derivatives containing two silyl groups as the electroauxiliaries. Introduction of two carbon nucleophiles into 2,6-position of piperidine was also successful. The products having two olefinic groups were effectively converted to nitrogen-containing spiro compounds using ring closing metathesis, and an application to formal synthesis of cephalotaxine was also carried out. These results clearly illustrate the synthetic utility and potential of the present approach, and open a new aspect of the synthesis of nitrogen-containing compounds.

Journal

  • Electrochemistry

    Electrochemistry 74 (8), 672-679, 2006

    The Electrochemical Society of Japan

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