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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (05): 707-712. 上一篇    下一篇

研究论文

壳聚糖及其L-脯氨酸衍生物催化的不对称Henry反应

崔元臣*,1,2，张和凤1，李润涛3，刘毅1，许楚1   

  1. (1河南大学化学化工学院 开封 475001)
    (2河南大学特种功能材料重点实验室 开封 475001)
    (3北京大学药学院 北京 100083)
  • 收稿日期:2009-08-11 修回日期:2009-10-25 发布日期:2009-12-15
  • 通讯作者: 崔元臣 E-mail:yccui@henu.edu.cn

Asymmetric Henry Reaction Catalyzed by Chitosan and Its L-Proline Derivative

Cui Yuanchen*,1,2 Zhang Hefeng1 Li Runtao3 Liu Yi1 Xu Chu1   

  1. (1 College of Chemistry and Chemical Engeering, Henan University, Kaifeng 47500)
    (2 Key Laboratory for Special Functionalal Materials, Ministry of Education, Henan University, Kaifeng 47500)
    (3 School of Pharmaceutical Sciences, Peking University, Bingjing 100083)
  • Received:2009-08-11 Revised:2009-10-25 Published:2009-12-15

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报道了壳聚糖负载L-脯氨酸化合物可以作为一种非均相有机催化剂在多种介质中有效催化多种底物的不对称Henry反应. 该催化剂在水及水溶胶束中表现出了比在有机溶剂中更高的催化活性. 实验中还意外发现壳聚糖本身对Henry反应也表现出了一定的催化活性, 并详细研究了不同条件下壳聚糖的催化性能. 同壳聚糖负载L-脯氨酸化合物一样, 壳聚糖本身在水和水溶胶束中表现出了比有机溶剂中更高的催化活性, 在Span-40水溶胶束中得到了99%的产率和1∶2.2的非对映选择性.

关键词: 壳聚糖, L-脯氨酸, 不对称Henry反应, 水, 水溶胶束

It was found that chitosan supported L-proline can be used as a heterogeneous organocatalyst to catalyze the asymmetric Henry reaction with different substrates in various media. The catalyst showed better performance in water and aqueous micelles. Unexpectedly, it was found that the chitosan itself can also catalyze Henry reaction. The catalytic performance of chitosan was well studied under various conditions. Similar to the chitosan supported L-proline, chitosan showed better performance in water and aqueous micelles than in the organic solvents, especially, a yield of 99% with a dr ratio of 1∶2.2 was obtained in Span-40 aqueous micelle.

Key words: chitosan, L-proline, asymmetric Henry reaction, water, aqueous micelle