A Facile Synthesis of N-[2-(Trifluoromethyl)allyl]amides and Their Transformation into Angularly Trifluoromethylated Bicyclic Cyclopentenones

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著者

    • NADANO Ryo
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • ICHIKAWA Junji
    • Department of Chemistry, Graduate School of Science, The University of Tokyo

抄録

On treatment with <I>sec</I>-BuLi at −105 °C, 2-bromo-3,3,3-trifluoropropene undergoes rapid lithium–halogen exchange to generate thermally unstable 1-(trifluoromethyl)vinyllithium, which reacts with <I>N</I>-tosylimines to afford <I>N</I>-[2-(trifluoromethyl)allyl]amides in high yield. Propargylation of the amides, followed by the Pauson–Khand reaction, readily provides pyrrolidine ring-fused cyclopentenones with an angular trifluoromethyl group.

収録刊行物

  • Chemistry letters

    Chemistry letters 36(1), 22-23, 2007-01-05

    The Chemical Society of Japan

参考文献:  19件中 1-19件 を表示

  • <no title>

    SHIMIZU M.

    Angew. Chem., Int. Ed. 44, 214, 2005

    被引用文献1件

  • <no title>

    LIN P.

    Tetrahedron, 2000

    被引用文献1件

  • <no title>

    DE MATTEIS V.

    J. Org. Chem. 71, 7527, 2006

    被引用文献1件

  • <no title>

    ICHIKAWA J.

    Chem. Lett. 33, 1354, 2004

    被引用文献1件

  • <no title>

    MORI T.

    Chem. Lett. 34, 778, 2005

    被引用文献1件

  • <no title>

    ICHIKAWA J.

    Synlett, 1998

    被引用文献1件

  • <no title>

    DRAKESMITH F. G.

    J. Org. Chem. 33, 280, 1968

    被引用文献1件

  • <no title>

    NADANO R.

    Synthesis, 2006

    被引用文献1件

  • <no title>

    CLAYDEN J. ed.

    Organolithiums : Selectivity for Synthesis, 2002

    被引用文献1件

  • <no title>

    BARHOUMI-SLIMI T.

    J. Fluorine Chem. 117, 137, 2002

    被引用文献1件

  • <no title>

    GIBSON S. E.

    Angew. Chem., Int. Ed. 44, 3022, 2005

    被引用文献1件

  • <no title>

    RIVERO M. R.

    Synlett, 2005

    被引用文献1件

  • <no title>

    RIVERO M. R.

    Eur. J. Org. Chem., 2002

    被引用文献1件

  • <no title>

    BONAGA L. V. R.

    Tetrahedron, 2004

    被引用文献1件

  • <no title>

    ISHIZAKI M.

    J. Fluorine Chem. 111, 81, 2001

    被引用文献1件

  • <no title>

    LEBEL H.

    Org. Lett. 4, 1671, 2002

    被引用文献1件

  • <no title>

    ICHIKAWA J.

    J. Org. Chem. 68, 7800, 2003

    被引用文献3件

  • <no title>

    ISEKI K.

    J. Fluorine Chem. 69, 5-6, 1994

    被引用文献2件

  • <no title>

    CASSAYRE J.

    J. Organomet. Chem. 624, 316, 2001

    被引用文献2件

各種コード

  • NII論文ID(NAID)
    10018662470
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    SHO
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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