Citation: Wenfang Wang, Qiangsheng Sun, Chungu Xia, Wei Sun. Enantioselective epoxidation of olefins with hydrogen peroxide catalyzed by bioinspired aminopyridine manganese complexes derived from L-proline[J]. Chinese Journal of Catalysis, ;2018, 39(9): 1463-1469. doi: 10.1016/S1872-2067(18)63116-X shu

Enantioselective epoxidation of olefins with hydrogen peroxide catalyzed by bioinspired aminopyridine manganese complexes derived from L-proline

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received Date: 26 March 2018
Revised Date: 22 May 2018

Fund Project: This work was supported by the National Natural Science Foundation of China (21473226, 21773273), Key Research Program of Frontier Sciences, CAS (QYZDJ-SSW-SLH051), and Natural Science Foundation of Jiangsu Province (BK20170420).

Three chiral aminopyridine ligands derived from L-proline were prepared. Careful evaluation of the corresponding aminopyridine manganese complexes in asymmetric epoxidation of olefins revealed a broad substrate scope in the presence of 0.2 mol% manganese complex and 0.5 equiv. 2,2-dimethylbutyric acid, with aqueous hydrogen peroxide as an oxidant. A variety of olefins including styrenes, chromenes, and cinnamamides were transformed successfully into the target epoxides with moderate to excellent enantioselectivity (yield up to 95%, ee up to 99%).
- Aminopyridine ligand,
- Manganese,
- Asymmetric epoxidation,
- Hydrogen peroxide,
- Olefin
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
32. [32]
33. [33]
34. [34]
35. [35]
36. [36]
37. [37]
1. [1]
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