Asymmetric Cleavage of 9-Azabicyclo[3.3.1]nonan-3-one into <I>cis</I>-2,6-Disubstituted Piperidine. A Facile Approach to a Chiral Building Block for Alkaloid Synthesis

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  • Momose Takefumi
    Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
  • Toyooka Naoki
    Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
  • Hirai Yoshiro
    Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

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Other Title
  • ChemInform Abstract: Asymmetric Cleavage of 9‐Azabicyclo(3.3.1)nona‐3‐one into cis‐2,6‐ Disubstituted Piperidine. A Facile Approach to a Chiral Building Block for Alkaloid Synthesis.

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Description

An asymmetric cleavage of the ‘fork head’ ketone of 9-azabicyclo[3.3.1]nonan-3-one gave a cis-2,6-disubstituted piperidine derivative in 93% ee, which was transformed to the cis-2,6-bis(hydroxymethyl)piperidine derivative, a versatile chiral building block.

Journal

  • Chemistry Letters

    Chemistry Letters 19 (8), 1319-1322, 1990

    The Chemical Society of Japan

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