Asymmetric Hydrosilylation of 1-Alkenes Catalyzed by Palladium-MOP

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著者

    • UOZUMI Yasuhiro
    • Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University
    • KITAYAMA Kenji
    • Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University
    • HAYASHI Tamio
    • Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University
    • FUKUYO Emiko
    • Tsukuba Research Laboratory, Sumitomo Chemical Co., Ltd.

抄録

Asymmetric hydrosilylation of simple terminal alkenes (RCH=CH<sub>2</sub>) with trichlorosilane at 40 °C in the presence of 1 × 10<sup>−3</sup> or 1 × 10<sup>−4</sup> molar amounts of palladium catalyst prepared in situ from [PdCl(<i>η</i><sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)]<sub>2</sub> and (<i>S</i>)-2-diphenylphosphino-2′-methoxy-1,1′-binaphthyl ((<i>S</i>)-MeO-MOP) proceeded with unusual regioselectivity and with high enantioselectivity to give high yields of 2-(trichlorosilyl)alkanes together with a minor amount of 1-(trichlorosilyl)alkanes. Optically active alcohols, RCH(OH)CH<sub>3</sub>, were obtained by oxidation of the carbon–silicon bond. Regioselectivities for forming 2-silylalkanes over 1-silylalkanes and enantiomeric purities of alcohols are as follows: R = <i>n</i>-C<sub>4</sub>H<sub>9</sub>: 89/11, 94% ee (<i>R</i>). R = <i>n</i>-C<sub>6</sub>H<sub>13</sub>: 93/7 95% ee (<i>R</i>). R = <i>n</i>-C<sub>10</sub>H<sub>21</sub>: 94/6, 95% ee (<i>R</i>). R = PhCH<sub>2</sub>CH<sub>2</sub>: 81/19, 97% ee (<i>S</i>). R = PhCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>: 80/20, 92% ee (<i>R</i>). R = <i>cyclo</i>-C<sub>6</sub>H<sub>11</sub>: 66/34, 96% ee (<i>R</i>). A similar hydrosilylation of 1-alkenes, 4-pentenyl benzoate and 1,5-heptadiene gave corresponding 2-alkanols of 90% ee and 87% ee, respectively, the ester carbonyl and the internal double bond remaining intact.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(3), 713-722, 1995-03-15

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10008887010
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
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  • ISSN
    00092673
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    CJP書誌  J-STAGE 
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