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有机化学 ›› 2010, Vol. 30 ›› Issue (10): 1521-1528. 上一篇    下一篇

研究论文

含三氟甲基的螺[环丙烷-1,3 -吲哚啉]-2 -酮和螺[环丙烷-1,2 -茚]-1 ,3 -二酮衍生物的高立体选择性简易合成

杨树新1，陈杰1，吴小余1，邓红梅2，邵敏2，张慧*,1，曹卫国*,1,3,4   

  1. (1上海大学化学系 上海 200444)
    (2上海大学分析测试中心 上海 200444)
    (3中国科学院上海有机化学研究所 金属有机化学国家重点开放实验室 上海 200032)
    (4中国科学院上海有机化学研究所 氟化学重点开放实验室 上海 200032)
  • 收稿日期:2010-01-25 修回日期:2010-05-05 发布日期:2010-06-02
  • 通讯作者: 张慧 E-mail:yehao7171@shu.edu.cn

Facile, Highly Stereoselective Synthesis of Spiro[cyclopropane-1,3 - indolin]-2 -ones and Spiro[cyclopropane-1,2 -indane]-1 ,3 -diones Containing Trifluoromethyl Group

Yang Shuxin1 Chen Jie1 Wu Xiaoyu1 Deng Hongmei2 Shao Min2 Zhang Hui*,1 Cao Weiguo*,1,3,4   

  1. (1 Department of Chemistry, Shanghai University, Shanghai 200444)
    (2 Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444)
    (3 State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
    (4 Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2010-01-25 Revised:2010-05-05 Published:2010-06-02

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采用3-(4-三氟甲基苯亚甲基)吲哚啉-2-酮和2-(4-三氟甲基苯亚甲基)-1H-茚-1,3(2H)-二酮分别与鉮盐在二氯甲烷中, 碳酸钾或氟化钾存在下反应, 可高产率、高立体选择性地得到以反式构型为主的含三氟甲基的3 -螺环丙基取代的氧化吲哚和2 -螺环丙基取代的茚二酮衍生物. 产物相对构型经X射线单晶衍射或1H-1H NOESY谱确定. 还从反应机理的角度对产物构型做了解释.

关键词: 螺环丙基, 氧化吲哚, 茚二酮, 胂叶立德, 立体选择性合成

In this paper, the new synthesis of trans-2,3-dihydro-spiro[cyclopropane-1,3 -indolin]-2 -one and trans-2,3-dihydro-spiro[cyclopropane-1,2 -indane]-1 ,3 -dione containing CF3 group was reported. Arsonium bromides 2 reacted with 2-(4-(trifluoromethyl)benzylidene)-1H-indene-1,3(2H)-dione (1) or 3-(4-(trifluoro- methyl)benzylidene)indolin-2-one (3), using KF or K2CO3 as base in CH2Cl2, to provide the target products with high stereoselectivity in good yields. The relative stereochemistry of key compounds has been determined by single-crystal X-ray structural analysis and 1H-1H NOESY technique. The mechanism was also proposed.

Key words: spirocyclopropyl, oxindole, 1,3-indandione, arsonium ylide, stereoselective synthesis