http://jcps.bjmu.edu.cn

• 研究论文 • 上一篇    下一篇

以1,2;4,5-二异亚丙基果糖为手性辅基非对应选择性合成1S-反式-环丙烷-1,2-二羧酸衍生物

李云锋, 孟祥豹*, 李庆, 李中军*
  

  1. 北京大学 天然药物及仿生药物国家重点实验室; 药学院 化学生物学系, 北京 100191
  • 收稿日期:2008-11-17 修回日期:2009-02-10 出版日期:2009-03-15 发布日期:2009-03-15
  • 通讯作者: 孟祥豹*, 李中军*

Diastereoselective synthesis of (1S)-trans-cyclopropane-1,2-dicarboxylic acid derivatives using 1,2;4,5-di-O-isopropylidene-D-fructopyranose as the chiral auxiliary

Yun-Feng Li, Xiang-Bao Meng*, Qing Li, Zhong-Jun Li*
  

  1. The State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
  • Received:2008-11-17 Revised:2009-02-10 Online:2009-03-15 Published:2009-03-15
  • Contact: Xiang-Bao Meng*, Zhong-Jun Li*

摘要: 发展了一种以果糖衍生物为手性辅基, 高立体选择性合成 (1S)-反式-环丙烷衍生物的方法。将手性辅基丙烯酰化再与叔胺反应生成铵盐, 用碳酸铯处理生成叶立德中间体, 引发环丙烷化反应。本论文提供了一种有效合成二取代或多取代手性环丙烷的方法。

关键词: 手性辅基, 糖, 不对称合成, 环丙烷化

Abstract:

A new procedure for the highly diastereoselective synthesis of (1S)-trans-cyclopropane derivatives using a fructose derivative as the chiral auxiliary was developed. Chloroacetylated 1,2;4,5-di-O-isopropylidene-D-fructopyranose was reacted with a tertiary amine to form the ammonium salt, which was treated with cesium carbonate to give the cyclopropane derivative through ylide intermediate. The described procedure provides an efficient method to synthesize optically pure di- or poly-substituded cyclopropanes.

Key words: Chiral auxiliary, Chiral auxiliary, Sugar, Sugar, Asymmetric synthesis, Asymmetric synthesis, Cyclopropanation, Cyclopropanation

中图分类号: 

Supporting: Foundation item: National Natural Science Foundation of China (Grant No. 20602001).
*Corresponding author. Tel.: 86-10-82801714