Magnesium Bromide-Promoted <I>E</I>⁄<I>Z</I>-Isomerization of Carbonyl-Conjugated Nitrones and Highly Stereo- and Regioselective Cycloadditions to Allylic Alcohol Dipolarophiles

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  • Kanemasa Shuji
    Institute of Advanced Material Study, Kyushu University
  • Tsuruoka Takashi
    Department of Molecular Science and Technology, Interdisciprinary Graduate School of Engineering Sciences, Kyushu University

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Other Title
  • ChemInform Abstract: Magnesium Bromide‐Promoted E/Z‐Isomerization of Carbonyl‐Conjugated Nitrones and Highly Stereo‐ and Regioselective Cycloadditions to Allylic Alcohol Dipolarophiles.

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Description

A Lewis acid promotes the E- to Z-isomerization of carbonyl-conjugated nitrones. The MgBr2•Et2O-catalyzed cycloadditions to allylic alcohols lead to the exclusive formation of the exo-stereoisomers of isoxazolidine-5-methanols. Participation of the Z-nitrone/MgBr2 complexes is suggested.

Journal

  • Chemistry Letters

    Chemistry Letters 24 (1), 49-50, 1995

    The Chemical Society of Japan

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