催化学报 ›› 2006, Vol. 27 ›› Issue (11): 946-948.

• 研究快讯 • 上一篇    下一篇

负载型双噁唑啉催化剂上的不对称Diels-Alder反应

王红1,刘健1,刘鹏1,杨启华1,肖建良2,李灿   

  1. 1 中国科学院大连化学物理研究所催化基础国家重点实验室, 辽宁大连 116023; 2 英国利物浦大学化学系, 利物浦 L69 7ZD, 英国
  • 收稿日期:2006-11-25 出版日期:2006-11-25 发布日期:2006-11-25

Asymmetric Diels-Alder Reactions on Supported Bis(Oxazoline) Catalysts

WANG Hong1, LIU Jian1, LIU Peng1, YANG Qihua1, XIAO Jianliang2, LI Can1*   

  1. 1 State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian 116023, Liaoning, China; 2 Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
  • Received:2006-11-25 Online:2006-11-25 Published:2006-11-25

摘要: 分别以乙烷桥键磺酸官能化的有机-无机杂化介孔材料、十二钨磷酸铯、活化硅胶以及SBA-15为载体,通过非共价键作用制备了负载型双噁唑啉催化剂,并将该催化剂用于催化3-((E)-2-丁烯酰基)-1,3-噁唑啉-2-酮和环戊二烯的不对称Diels-Alder反应. 研究表明,催化剂的性能取决于载体本身以及载体表面阴离子的性质. 以SBA-15为载体时产物的对映体选择性较低,可归因于载体表面较低的羟基浓度.

关键词: 负载型催化剂, 双噁唑啉络合物, Diels-Alder反应, 活化硅胶, SBA-15

Abstract: Periodic mesoporous ethane-silicas functionalized with sulfonic acid, cesium salts of 12-tungstophosphoric acid, activated silica, and SBA-15 have been used as solid supports for the immobilization of the bis(oxazoline) copper (Ⅱ) catalyst via non-covalent interactions. These heterogeneous catalysts have been evaluated for the Diels-Alder reaction between 3-((E)-2-butenoyl)-1,3-oxazolin-2-one and cyclopentadiene. The performance of the catalyst relies on the nature of both the support and the anion on the surface of the support. The small number of the silanol groups on the support leads to poor enantioselectivity when SBA-15 is used.

Key words: supported catalyst, bis(oxazoline) complex, Diels-Alder reaction, activated silica, SBA-15