Citation: Zhu Qingying, Shen Haimin, Ji Hongbing. Asymmetric Epoxidation of trans-Chalcone by H₂O₂ Induced by β-Cyclodextrin Derivatives in Water[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1907-1914. doi: 10.6023/cjoc201512022 shu

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

Zhu Qingying ^a,b ,
Shen Haimin ^c ,
Ji Hongbing ^a,*,,

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

Corresponding author: Ji Hongbing, jihb@mail.sysu.edu.cn
Received Date: 17 December 2015
Revised Date: 19 February 2016

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

Figures(6)

Six amino-alcohol modified β-cyclodextrins CD-1～CD-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 H₂O₂and 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-1～CD-6, which affected the enhancement of the ee value. And the two kinds of inclusion complexes were confirmed by quantum chemistry calculation too.
- β-cyclodextrin,
- asymmetry,
- epoxidation,
- trans-chalcone
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Asymmetric Epoxidation of trans-Chalcone by H₂O₂ Induced by β-Cyclodextrin Derivatives in Water