含窒素複素環式カルベン化学の新展開 : 有機触媒としての利用 New Developments in the N-Heterocyclic Carbene Chemistry : Application as Organocatalysts

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N-heterocyclic carbenes have been studied for their abilities to catalyze C-C bond formation/cleavage and asymmetric reactions. N-heterocyclic carbenes generated from imidazolium, benzimidazolium, triazolium, pyrido[1, 2-c]imidazolium, pyrido[2, 1-c]triazolium, and dipyrido[1, 2-c : 2'1'-e]imidazolium iodide were found to be effective catalysts in benzoin condensation. The acidity of the azolium salts at the C2-hydrogen of the imidazolium or the triazolium moieties relates to the base effect on the reaction. These carbenes can also be employed in retro-benzoin condensation, which is a new method of synthesizing ketones by C-C bond cleavage of α-substituted benzoins. Chloro and fluoro groups of haloarenes are nucleophilically substituted by aroyl groups originated from aromatic aldehydes by catalytic action of imidazolidenyl and triazolidenyl carbenes to afford ketones. N-heterocyclic carbenes mediate the addition of trimethylsilylcyanide to aldehydes to yield cyanohydrin trimethylsilyl ethers. The use of chiral imidazolidenyl carbene derived from (R, R)-1, 3-bis[(1-naphthyl)ethyl] imidazolium chloride led to enantioseletive cyanosilylation. C<SUB>2</SUB>-symmetric imidazolidenyl carbenes catalyze asymmetric acylation of racemic secondary alcohols.

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 66(4), 377-386, 2008-04-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10021174718
  • 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
    9460125
  • 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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