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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (07): 815-820. 上一篇    下一篇

研究论文

连二亚硫酸钠引发的手性2-取代-4-戊烯酸的氟烷基化反应研究

杨雪艳1，吕铁梅1，朱胜杰1，吴范宏*,2,3   

  1. (1华东理工大学化学与分子工程学院 上海 200237)
    (2上海应用技术学院化学与环境工程学院 上海 200235)
    (3中国科学院上海有机化学研究所有机氟化学重点实验室 上海 200032)
  • 投稿日期:2010-07-08 修回日期:2010-11-17 发布日期:2010-12-06
  • 通讯作者: 杨雪艳 E-mail:yangxy_2008@hotmail.com
  • 基金资助:

    国家自然科学基金项目

Fluoroalkylation of Chiral Enoic Acids Initiated by Sodium Dithionite

Yang Xueyan1 Lü Tiemei1 Zhu Shengjie1 Wu Fanhong*,2,3   

  1. (1 School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237)
    (2 Chemical and Environmental Engineering Institute, Shanghai Institute of Technology, Shanghai 200237)
    (3 Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2010-07-08 Revised:2010-11-17 Published:2010-12-06
  • Contact: Xue-Yan Yang E-mail:yangxy_2008@hotmail.com

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被引次数

5

研究了手性4-戊烯酸衍生物的氟烷基化反应. 以连二亚硫酸钠为引发剂, 在碱作用下, 乙腈水溶液中手性4-戊烯酸与含氟碘代烷一锅法反应得到手性含氟γ-丁内酯. 其结构经核磁共振、高分辨质谱、红外光谱确定. 其绝对构型经单晶衍射确定.

关键词: 手性烯酸, 氟烷基化, 连二亚硫酸钠, 手性含氟内酯

The fluoroalkylation reaction of chiral 4-pentenoic acids with RFI was investigated. In aqeous acetonitrile, chiral 4-pentenoic acids reacted with fluoroalkyl iodide initiated by sodium dithitionite in the presence of base to afford chiral fluorine-containing γ-butyrolactones. The structures of the compounds were comfirmed by NMR, IR, and HRMS techniques. The configurations were ascertained by X-ray single crystal diffraction.

Key words: chiral enoic acid, fluoroalkylation, sodium dithionite, chiral fluorine-containing γ-buty- rolactone