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

doi:10.6023/cjoc201512022

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

ARTICLE

β-环糊精衍生物诱导H₂O₂水相不对称环氧化trans-查尔酮

朱庆英^a,b, 沈海民^c, 纪红兵^a

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 E-mail:jihb@mail.sysu.edu.cn
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 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

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).

1. Asymmetric Epoxidation of trans-Chalcone by H₂O₂ Induced by β-Cyclodextrin Derivatives in Water.PDF(748KB)

Abstract

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.

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

Cite this article

Zhu Qingying, Shen Haimin, Ji Hongbing. Asymmetric Epoxidation of trans-Chalcone by H₂O₂ Induced by β-Cyclodextrin Derivatives in Water[J]. Chin. J. Org. Chem., 2016, 36(8): 1907-1914.

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β-环糊精衍生物诱导H₂O₂水相不对称环氧化trans-查尔酮

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

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β-环糊精衍生物诱导H2O2水相不对称环氧化trans-查尔酮