壳聚糖负载辛可宁催化剂的制备及其在水中催化不对称Aldol反应

doi:10.1016/S1872-2067(14)60248-5

催化学报 ›› 2015, Vol. 36 ›› Issue (3): 367-371.DOI: 10.1016/S1872-2067(14)60248-5

壳聚糖负载辛可宁催化剂的制备及其在水中催化不对称Aldol反应

赵文善^a, 曲程科^a, 杨莉莉^a, 崔元臣^b

a 河南大学化学化工学院, 河南开封475004;
b 河南大学特种功能材料教育部重点实验室, 河南开封475004

收稿日期:2014-09-04 修回日期:2014-10-10 出版日期:2015-02-14 发布日期:2015-02-14
通讯作者: 崔元臣

Chitosan- supported cinchonine as an efficient organocatalyst for direct asymmetric aldol reaction in water

Wenshan Zhao^a, Chengke Qu^a, Lili Yang^a, Yuanchen Cui^b

a College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, Henan, China;
b Key Laboratory of Ministry of Education for Special Functional Materials, Henan University, Kaifeng 475004, Henan, China

Received:2014-09-04 Revised:2014-10-10 Online:2015-02-14 Published:2015-02-14

摘要/Abstract

摘要：

以丁二酸酐为连接臂, 经两步反应制备了壳聚糖负载辛可宁有机催化剂(CTS-SA-CN), 并研究了CTS-SA-CN在水体系中对酮与多种芳香醛的直接不对称aldol反应的催化性能.结果表明, 在CTS-SA-CN催化下, 酮与多种芳香醛发生直接不对称aldol反应, 可得到99%的产率和96%的ee值.另外, CTS-SA-CN可通过简单过滤实现回收, 重复使用5次活性并没有明显下降.

关键词: 壳聚糖, 辛可宁, 负载型催化剂, 直接不对称Aldol反应

Abstract:

Chitosan-supported succinic anhydride-cinchonine (CTS-SA-CN) was synthesized via a two-step route with succinic anhydride as the linker. The catalyst was used to promote the direct asymmetric aldol reaction between cyclohexanone and a variety of aromatic aldehydes in aqueous medium. Aldol adducts were obtained in excellent yields (up to 99%) and good enantioselectivities (up to 96% ee). The CTS-SA-CN catalyst was successfully recycled simply by filtration after use, and was reused 5 times without any significant loss of activity.

Key words: Chitosan, Cinchonine, Supported catalyst, Direct asymmetric aldol reaction

赵文善, 曲程科, 杨莉莉, 崔元臣 . 壳聚糖负载辛可宁催化剂的制备及其在水中催化不对称Aldol反应[J]. 催化学报, 2015, 36(3): 367-371.

Wenshan Zhao, Chengke Qu, Lili Yang, Yuanchen Cui. Chitosan- supported cinchonine as an efficient organocatalyst for direct asymmetric aldol reaction in water[J]. Chinese Journal of Catalysis, 2015, 36(3): 367-371.

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壳聚糖负载辛可宁催化剂的制备及其在水中催化不对称Aldol反应

Chitosan- supported cinchonine as an efficient organocatalyst for direct asymmetric aldol reaction in water

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