パラジウム錯体触媒による置換アレン類の立体選択的合成法の開発とその応用 Palladium-Catalyzed Stereoselective Synthesis of Multisubstituted Allenes and Their Application in Organic Transformations

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A novel Pd-catalyzed reaction of a 2-halo- or 2-trifloxy-l, 3-butadiene derivative with a soft nucleophile is developed. The reaction proceeds via an exo-alkylidene-π-allylpalladium intermedi-ate in a formal SN2' fashion to give an allenic compound exclusively. A variety of soft nucleophiles, such as malonates, phenoxides, and imides, are applicable to the reaction, and thus a wide range of functionality can be introduced to the products. The reaction is extended into an asymmetric counterpart and axially chiral allenes are prepared with up to 93% ee by the use of chiral palladium catalysts. A formal total synthesis of an insect pheromone is achieved using the Pd-catalyzed asymmetric reaction as a key step. The Pd-catalyzed reaction also enables to prepare axially chiral (allenylmethyl) silanes and allenylsilanes in optically active forms. Reactions of these silylallenes with appropriate electrophiles proceed via SE', pathways and the allenic axial chirality is efficiently transferred to stereogenic carbon centers in the SE', products.

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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 66(2), 100-109, 2008-02-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10021173451
  • 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
    9378857
  • 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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