Enantioselective cyclopropanation reactions with planar-chiral pyridinium ylides: A substituent effect and a remote steric effect

Nobuhiro Kanomata, Ryo Sakaguchi, Kazuki Sekine, Satomi Yamashita, Hiroko Tanaka

    研究成果: Article

    24 引用 (Scopus)

    抄録

    Novel planar-chiral pyridinium ylides were designed, and generated in situ from the corresponding pyridinium salts with triethylamine. Ylides with a common parapyridinophane skeleton reacted efficiently with electron-deficient dicyanoalkenes, or malononitriles, to produce optically active cyclopropane derivatives with high enantioselectivity (up to 99% ee). Remote steric effects were observed on the enantioselectivities, where the R2 groups of the pyridinophane core resulted in higher ee values of the products. Density function theory (DFT) calculations are in good agreement with our experimental results: the energetically favored transition state leads to the major stereoisomer, namely the trans-cyclopropane products.

    元の言語English
    ページ(範囲)2966-2978
    ページ数13
    ジャーナルAdvanced Synthesis and Catalysis
    352
    発行部数17
    DOI
    出版物ステータスPublished - 2010 11 22

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    Enantioselectivity
    Stereoisomerism
    Probability density function
    Salts
    Derivatives
    Electrons
    cyclopropane
    dicyanmethane
    triethylamine

    ASJC Scopus subject areas

    • Catalysis
    • Organic Chemistry

    これを引用

    Enantioselective cyclopropanation reactions with planar-chiral pyridinium ylides : A substituent effect and a remote steric effect. / Kanomata, Nobuhiro; Sakaguchi, Ryo; Sekine, Kazuki; Yamashita, Satomi; Tanaka, Hiroko.

    :: Advanced Synthesis and Catalysis, 巻 352, 番号 17, 22.11.2010, p. 2966-2978.

    研究成果: Article

    Kanomata, Nobuhiro ; Sakaguchi, Ryo ; Sekine, Kazuki ; Yamashita, Satomi ; Tanaka, Hiroko. / Enantioselective cyclopropanation reactions with planar-chiral pyridinium ylides : A substituent effect and a remote steric effect. :: Advanced Synthesis and Catalysis. 2010 ; 巻 352, 番号 17. pp. 2966-2978.
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    AU - Kanomata, Nobuhiro

    AU - Sakaguchi, Ryo

    AU - Sekine, Kazuki

    AU - Yamashita, Satomi

    AU - Tanaka, Hiroko

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