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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (08): 1222-1229. 上一篇    下一篇

研究论文

(5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮与氨基酸的串联反应

谭越河1，汪朝阳*,1，郝志峰2，李建晓1   

  1. (1 华南师范大学化学与环境学院 广州 510006)
    (2 广东工业大学轻工化工学院 广州 510006)
  • 收稿日期:2011-01-26 修回日期:2011-03-06 发布日期:2011-03-21
  • 通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com

Tandem Reaction of (5S)-5-Alkoxy-3,4-dihalo-5H-furan-2-ones with Amino Acids

Tan Yuehe1 Wang Zhaoyang*,1 Hao Zhifeng2 Li Jianxiao1   

  1. (1 School of Chemistry and Environment, South China Normal University, Guangzhou 510006)
    (2 Faculty of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006)
  • Received:2011-01-26 Revised:2011-03-06 Published:2011-03-21
  • Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com

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在氢氧化钾作用下, 直接以不同种类氨基酸为亲核试剂, 与手性(5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮在室温下进行串联的不对称迈克尔加成-消除反应, 合成了15个新的光学活性2(5H)-呋喃酮衍生物. 通过旋光度, UV-Vis, IR, 1H NMR, 13C NMR, MS, 元素分析和X射线单晶衍射等表征方法, 确定了目标化合物的化学结构和绝对构型.

关键词: (5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮, 氨基酸, 串联迈克尔加成-消除反应, 光学活性, 多手性中心

Different kinds of amino acids, directly serving as nucleophiles, were reacted with (5S)-5-alkoxy-3,4-dihalo-5H-furan-2-ones via tandem asymmetric Michael addi-tion-elimination in the presence of potassium hydroxide to give 15 new optically active 5H-furan-2-one derivatives. The chemical structures and absolute configurations of these compounds were confirmed via rotation, UV-Vis, IR, 1H NMR, 13C NMR, MS, elemental analysis and X-ray single crystal diffraction.

Key words: (5S)-5-alkoxy-3,4-dihalo-5H-furan-2-one, amino acid, tandem Michael addi-tion-elimination, optical activity, multiple chiral center