Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1907-1914.DOI: 10.6023/cjoc201512022 Previous Articles     Next Articles



朱庆英a,b, 沈海民c, 纪红兵a   

  1. a 中山大学化学与化学工程学院 广州 510275;
    b 惠州学院化工系 惠州 516007;
    c 浙江工业大学化学工程学院 杭州 310014
  • 收稿日期:2015-12-17 修回日期:2016-02-19 发布日期:2016-04-05
  • 通讯作者: 纪红兵
  • 基金资助:

    国家杰出青年科学基金(No. 21425627)资助项目.

Asymmetric Epoxidation of trans-Chalcone by H2O2 Induced by β-Cyclodextrin Derivatives in Water

Zhu Qingyinga,b, Shen Haiminc, Ji Hongbinga   

  1. a School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275;
    b Department of Chemical Engineering, Huizhou College, Huizhou 516007;
    c College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
  • Received:2015-12-17 Revised:2016-02-19 Published:2016-04-05
  • Supported by:

    Project supported by the National Science Fund for Distinguished Young Scholars (No. 21425627).

Six amino-alcohol modified β-cyclodextrins CD-1CD-6 were synthesized by nucleophilic substitution from mono(6-O-p-tolylsulfonyl)-β-cyclodextrin with the yields of 34%~58%, and were verified by 1H NMR, 13C NMR and ESI-MS techniques. These β-cyclodextrin derivatives were applied to the asymmetric epoxidation of trans-chalcone by H2O2. And the results implied that the dosage of the β-cyclodextrin derivatives and the structure of the modified group had an important effect on the enantioselectivity in the reaction. Among them, CD-1 exhibited the best performance in the asymmetric epoxidation of trans-chalcone employed H2O2 and NaHCO3 as oxidant, and 25.7% ee value was obtained. It were showed from the spectra of 2D-1H ROESY NMR that, CD-1 could form inclusion complex with trans-chalcone and self-inclusion existed in all the β-cyclodextrin derivatives CD-1CD-6, which affected the enhancement of the ee value. And the two kinds of inclusion complexes were confirmed by quantum chemistry calculation too.

Key words: β-cyclodextrin, asymmetry, epoxidation, trans-chalcone