Desymmetrization of 1,4-Pentadien-3-ol by the Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines

Authors

  • Mari Yoshida,

    1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742
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  • Naotaro Sassa,

    1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742
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  • Tomomitsu Kato,

    1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742
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  • Dr. Shuhei Fujinami,

    1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742
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  • Dr. Takahiro Soeta,

    1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742
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  • Prof. Dr. Katsuhiko Inomata,

    1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742
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  • Prof. Dr. Yutaka Ukaji

    Corresponding author
    1. Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742
    • Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192 (Japan), Fax: (+81) 76-264-5742

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Abstract

Desymmetrization of the divinyl carbinol 1,4-pentadien-3-ol was accomplished by the asymmetric 1,3-dipolar cycloaddition of azomethine imines based on a magnesium-mediated, multinucleating chiral reaction system utilizing diisopropyl (R,R)-tartrate as the chiral auxiliary. The corresponding optically active trans-pyrazolidines, each with three contiguous stereogenic centers, were obtained with excellent regio-, diastereo-, and enantioselectivity, with results as high as 99 % ee. This reaction was shown to be applicable to both aryl- and alkyl-substituted azomethine imines. The use of a catalytic amount of diisopropyl (R,R)-tartrate was also effective when accompanied by the addition of MgBr2.

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