複素芳香族化合物インドールの触媒的不斉水素化 Catalytic Asymmetric Hydrogenation of Heteroaromatic Compounds, Indoles

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著者

    • 桑野 良一 KUWANO Ryoichi
    • 九州大学大学院理学研究院化学部門 Department of Chemistry, Graduate School of Sciences, Kyushu University

抄録

Catalytic asymmetric hydrogenation of olefins, ketones, and imines has widely been used to prepare various optically active compounds. Meanwhile, few asymmetric hydrogenations of aromatic groups had been reported until recently. We found hydrogenation of indoles to proceed with high enantioselectivity in the presence of a rhodium catalyst modified with a trans-chelating chiral ligand PhTRAP. The rhodium catalyst transformed <I>N</I>-acetylindoles bearing a substituent at 2-position into the corresponding indolines with up to 95% ee. 3-Substituted indoles were hydrogenated with high enantioselectivity (up to 98% ee) when their nitrogen was protected with a sulfonyl group. A PhTRAP-ruthenium catalyst exhibited high enantioselectivity (up to 95% ee) for the hydrogenation of <I>N</I>-Boc-indoles. The ruthenium complex catalyzed the hydrogenation of 2, 3-disubstituted indoles as well as 2- or 3-monosubstituted indoles. Furthermore, the recent progress of asymmetric hydrogenation of aromatic compounds was surveyed in this paper.

収録刊行物

  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN  

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 65(2), 109-118, 2007-02-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10018497050
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    ART
  • ISSN
    00379980
  • NDL 記事登録ID
    8683433
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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