Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1456-1459.DOI: 10.6023/cjoc201810029 Previous Articles     Next Articles

Notes

手性联萘酚聚合物在不对称环氧化反应中的应用

蔡瀚, 欧阳昆冰, 阳年发   

  1. 湘潭大学化学学院 环境友好化学与应用省部共建教育部重点实验室 湘潭 411105
  • 收稿日期:2018-10-24 修回日期:2019-01-16 出版日期:2019-05-25 发布日期:2019-03-08
  • 通讯作者: 欧阳昆冰, 阳年发 E-mail:kbouyang@xtu.edu.cn;nfyang@xtu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21602188)、湖南省教育厅一般项目(No.17C1524)、湘潭大学博士科研启动基金(No.15QDZ52)资助项目.

Application of Chiral 1,1'-Bi-2-naphthol Polymers in Asymmetric Epoxidation of (E)-α,β-Unsaturated Aryl Ketones

Cai Han, Ouyang Kunbing, Yang Nianfa   

  1. Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105
  • Received:2018-10-24 Revised:2019-01-16 Online:2019-05-25 Published:2019-03-08
  • Contact: 10.6023/cjoc201810029 E-mail:kbouyang@xtu.edu.cn;nfyang@xtu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21602188), the Education Department of Hunan Province (No. 17C1524) and the Doctoral Research Initiation Fund of Xiangtan University (No. 15QDZ52).

Most small chiral molecule catalysts are suffered from a rigid process in both product separation and recovery. Therefore more attention has been drawn to the soluble polymer-supported catalyst which could be easily recycled. In this paper, a new type of reusable chiral binaphthol polymer-supported diethylzinc catalyst was synthesized and applied in the asymmetric epoxidation of (E)-α,β-unsaturated aryl ketones. The scope of this reaction was explored. Various (E)-α,β-aryl ketones could be easily prepared in good yield (up to 88%) and high ee value (up to 94%) via this asymmetric epoxidation process. Ligands were recovered to explore the inductive effect of the reaction. Recovery experiments of this binaphthol polymer-supported diethylzinc catalyst were conducted. The results indicate that the asymmetric induction ability of the reclaimed chiral polymer 1,1'-bi-2-naphthol did not decrease significantly.

Key words: 1,1'-bi-2-naphthol, Et2Zn, chiral polymer, asymmetric addition, aromatic ketone