催化学报

催化学报 ›› 2012, Vol. 33 ›› Issue (3): 473-477.DOI: 10.1016/S1872-2067(11)60345-8

• 研究论文 • 上一篇    下一篇

聚甲基丙烯酸羟乙酯负载手性 Mn(III)salen 配合物催化 α-甲基苯乙烯的不对称环氧化反应

徐国津 1,2, 魏赛丽 2, 樊颖果 1, 朱丽波 1, 唐玉海 2,*, 郑元锁 2   

  1. 1 宁波市环境监测中心, 浙江宁波 315012; 2 西安交通大学理学院分析科学研究所, 陕西西安 710061
  • 收稿日期:2011-09-08 修回日期:2011-11-22 出版日期:2012-03-15 发布日期:2015-07-27

A Poly(hydroxyethyl methacrylate)-Immobilized Chiral Manganese(III)salen Catalyst for Asymmetric Epoxidation of α-Methylstyrene

XU Guojin1, WEI Saili2, FAN Yingguo1, ZHU Libo1, TANG Yuhai2,*, ZHENG Yuansuo2   

  1. 1Environment Monitoring Center of Ningbo, Ningbo 315012, Zhejiang, China; 2Institute of Analytical Sciences, School of Science, Xi’an Jiaotong University, Xi’an 710061, Shaanxi, China
  • Received:2011-09-08 Revised:2011-11-22 Online:2012-03-15 Published:2015-07-27

PDF

928

摘要： 在手性 Mn(III)salenCl 配合物的 5 和 5'位上引入氨基醇, 将其通过轴配位作用负载于聚甲基丙烯酸羟乙酯 (pHEMA) 上, 并用于离子液体[bmim]PF6 中, 催化 α-甲基苯乙烯的不对称环氧化反应. 结果表明, 该催化剂表现出良好的催化活性和区域选择性, 对映体过量值 (ee) 和产率可分别达 80%~91% 和 84%~92%, 循环使用 5 次后催化活性没有明显降低. 这可归结为氨基醇和环己二胺中手性碳原子间相互协同作用.

关键词: 聚甲基丙烯酸羟乙酯, 负载型 Mn(III)salen, 不对称环氧化, α-甲基苯乙烯, 离子液体

Abstract: Phenylalaninol was introduced in the C5 and C5′ position of a chiral Mn(III)salenCl compound, and the catalyst was then immobilized on poly(hydroxyethyl methacrylate) (pHEMA) by axial coordination. The catalytic system, with (R,R)(R,R)pHEMA-immobilized Mn(III)salenCl as catalyst and [bmim]PF6 as reaction medium, gave excellent catalytic activity and enantioselectivity with 80%–91% ee values and 84%–92% yields for the asymmetric epoxidation of α-methylstyrene. The catalyst can be reused several times without significant loss of catalytic activity. This was due to a chiral synergy between the chiral carbons of the amino alcohol and the chiral carbons of (R,R)-diaminocyclohexane.

Key words: poly(hydroxyethyl methacrylate), immobilized Mn(III)salen, asymmetric epoxidation, α-methylstyrene, ionic liquid