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Citation: Ruxia Yi, Leilei Qian, Boshun Wan. Synthesis of spiropyrrolidine oxindoles through Rh(II)-catalyzed olefination/cyclization of diazooxindoles and vinyl azides[J]. Chinese Journal of Catalysis, ;2019, 40(2): 177-183. doi: 10.1016/S1872-2067(18)63200-0 shu

Synthesis of spiropyrrolidine oxindoles through Rh(II)-catalyzed olefination/cyclization of diazooxindoles and vinyl azides

Ruxia Yi ^a,b, ,
Leilei Qian ^a,b ,
Boshun Wan ^a

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received Date: 2 November 2018
Revised Date: 14 November 2018

Fund Project: This work was supported by the National Natural Science Foundation of China (21572225).

A simple and efficient process involving the Rh(Ⅱ)-catalyzed[1+1+3] annulation of diazooxindoles and vinyl azides has been developed for the synthesis of spiropyrrolidine oxindoles with potential biological activity and significant synthetic applications. This process involves a novel rhodium-catalyzed olefination of diazo compounds, followed by annulation with vinyl azides. This method is compatible with a broad range of substrates and affords moderate to good yields under mild reaction conditions.
- Rhodium catalyst,
- Vinyl azides,
- Diazo compounds,
- Spiropyrrolidine oxindoles,
- Olefination,
- [1+1+3] annulation
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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