環隣接位に不斉中心を有する光学活性ピリジン類の合成 Synthesis of Optically Active Pyridines with a Chiral Center at the Next Position to the Ring

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Chiral compounds containing a pyridine unit have been used widely for many functional molecules including ligands for molecular recognition chemistry and catalytic asymmetric reactions and medicines. In this review, the synthesis of chiral non-racemic pyridinylethyl units and some functional molecules that have the units are described. Our synthetic approach involves a lipase catalyzed acetylation of pyridinyl alcohols and a stereospecific subsitution of their methane-sulfonates with <I>N</I>-, <I>S</I>-, <I>O</I>-, and <I>C</I>-nucleophiles. Although a nucleophilic substitution reaction on the benzylic position has been extensively investigated, there have been few studies of that on the pyridinylmethyl position. We have revealed that perfect stereospecific substitutions occur in the reaction of non-racemic 1- (2-pyridinyl) ethyl methanesulfonates with various nucleophiles through a S<I>N</I>2 process. A number of optically pure chiral non-racemic 1- (2-pyridinyl) ethyl derivatives were synthesized.

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  • 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), 127-138, 2007-02-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10018497128
  • 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
    8683450
  • 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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