Enantioselective epoxidation of unfunctionalized olefins by Jacobsen's catalyst immobilized on amino-modified ZnPS-PVPA

doi:10.1016/S1872-2067(16)62489-0

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (9): 1539-1549.DOI: 10.1016/S1872-2067(16)62489-0

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Enantioselective epoxidation of unfunctionalized olefins by Jacobsen's catalyst immobilized on amino-modified ZnPS-PVPA

Jing Huang^a,b, Yan luo^c, Jiali Cai^d

a. Research Center for Advanced Computation, Xihua University;College of Science, Xihua University, Chengdu 610039, Sichuan, China;
b. Institute for Clean Energy & Advanced Materials, Southwest University, Chongqing 400715, China;
c. College of Materials and Chemical Engineering, Chongqing University of Arts and Science, Chongqing 402160, China;
d. College of Rongchang, Southwest University, Chongqing 402460, China

Received:2016-04-28 Revised:2016-05-28 Online:2016-09-21 Published:2016-09-21
Contact: Jing Huang
Supported by:
This work was supported by the Fundamental Research Funds for the Central Universities(XDJK2013C120), Xihua University Key Projects(Z1223321), Sichuan Province Applied Basic Research Projects(2013JY0090), Department of Education of Sichuan Province Projects(13ZB0030), Chongqing Special Funding for Postdoctoral(Xm2014028), Chongqing Postdoctoral Daily Fund(Rc201419), and Scientific and Technological Research Program of Chongqing Municipal Education Commission(KJ1501127).

Abstract

Abstract:

Catalytic asymmetric epoxidation of alkenes is a powerful method for the synthesis of chiral organic compounds. A recyclable chiral Jacobsen's catalyst immobilized on ZnPS-PVPA on diamines gave high catalytic activity(conversion > 99%, ee > 99%) in the asymmetric epoxidations of unfunctionalized olefins. The synergistic effect of the support ZnPS-PVPA and the linkage as well as chiral salen Mn center contributed to the chirality of the product. The stability(recycled nine times) and the ease of use in large scale reactions(200 times scale) indicated a catalyst useful for industrial use.

Key words: Chiral salen Mn(Ⅲ), Aryldiamine, Alkyldiamine, Asymmetric epoxidation of olefins, Zinc poly(styrene-phenylvinylphosphonate)-phosphate

Jing Huang, Yan luo, Jiali Cai. Enantioselective epoxidation of unfunctionalized olefins by Jacobsen's catalyst immobilized on amino-modified ZnPS-PVPA[J]. Chinese Journal of Catalysis, 2016, 37(9): 1539-1549.

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Enantioselective epoxidation of unfunctionalized olefins by Jacobsen's catalyst immobilized on amino-modified ZnPS-PVPA

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