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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (12): 1890-1897. 上一篇    下一篇

研究论文

无保护α-氨基酸合成多手性中心2(5H)-呋喃酮化合物

宋秀美1,2，谭越河1，李建晓1，汪朝阳*,1   

  1. (1华南师范大学化学与环境学院 广州 510006)
    (2湛江师范学院 化学科学与技术学院 化学与材料研究中心
    广东高校新材料工程技术开发中心 湛江 524048)
  • 收稿日期:2010-05-26 修回日期:2010-07-06 发布日期:2010-07-23
  • 通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com

Synthesis of 5H-Funan-2-ones with Multiple Chiral Centers Directly from Unprotected α-Amino Acids

Song Xiumei1,2 Tan Yuehe1 Li Ji-anxiao1 Wang Zhaoyang*,1   

  1. (1 School of Chemistry and Environment, South China Normal University, Guangzhou 510006)
    (2 Research Center of Chemistry and Marterials, Development Center for New Ma-terials Engineering & Technology in Universities of Guangdong, Chemistry Science and Technology School, Zhanjiang Normal College, Zhanjiang 524048)
  • Received:2010-05-26 Revised:2010-07-06 Published:2010-07-23
  • Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com

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以无保护的α-氨基酸为亲核试剂, 与不同的手性(5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮进行串联的迈克尔加成-消除反应, 合成了15个新的光学活性2(5H)-呋喃酮衍生物. 利用旋光度, 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, 确定了新的多手性中心2(5H)-呋喃酮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, 无保护α-氨基酸, 串联迈克尔加成-消除反应, 光学活性, 多手性中心

Five unprotected α-amino acids, serving as nucleophiles, were reacted with different (5S)-5- alkoxy-3,4-dihalo-5H-furan-2-ones via tandem Michael addition-elimination to give 15 new optically active 5H-furan-2-one derivatives. The chemical structures and absolute configurations of these compounds with multiple chiral centers 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, unprotected α-amino acid, tandem Michael addition-elimination, optical activity, multiple chiral center