Citation: Cao Shi-Xuan, Wang Jia-Xi, He Zheng-Jie. Magnetic nanoparticles supported cinchona alkaloids for asymmetric Michael addition reaction of 1, 3-dicarbonyls and maleimides[J]. Chinese Chemical Letters, ;2018, 29(1): 201-204. doi: 10.1016/j.cclet.2017.06.022 shu

Magnetic nanoparticles supported cinchona alkaloids for asymmetric Michael addition reaction of 1, 3-dicarbonyls and maleimides

a.
School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, China
b.
The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
c.
Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300071, China

Corresponding author: Wang Jia-Xi, wangjiaxi@hebut.edu.cn He Zheng-Jie, zhengjiehe@nankai.edu.cn
Received Date: 29 April 2017
Revised Date: 4 June 2017
Accepted Date: 22 June 2017
Available Online: 26 January 2017

Figures(3)

Magnetic nanoparticles Fe₃O₄@SiO₂ supported cinchona alkaloids (quinine and quinidine) were successfully synthesized as magnetically recoverable organocatalysts and characterized by FT-IR, XPS, SEM measurements, and elemental analysis. Their catalytic activity and stereoselectivity were preliminarily evaluated in the asymmetric Michael addition reaction of 1, 3-dicarbonyls and maleimides. The supported quinine catalyst exhibited good catalytic efficiency and modest to high enantioselectivity. The magnetic recoverability and recyclability of the catalyst were also examined.
- Magnetic nanoparticles,
- Cinchona alkaloids,
- Immobilization,
- Michael addition,
- Asymmetric catalysis
1. [1]
  K. Kacprzak, J. Gawronski, Synthesis (2001) 961-998.
2. [2]
  E.M.O. Yeboah, S.O. Yeboah, G.S. Singh, Tetrahedron 67(2011) 1725-1762. doi: 10.1016/j.tet.2010.12.050
3. [3]
  J.D. Duan, P.F. Li, Catal. Sci. Technol. 4(2014) 311-320. doi: 10.1039/C3CY00739A
4. [4]
  L. Jiang, Y.-C. Chen, Catal. Sci. Technol. 1(2011) 354-365. doi: 10.1039/c0cy00096e
5. [5]
  P.F. Zheng, Q. Ouyang, S.L. Niu, et al., J. Am. Chem. Soc. 137(2015) 9390-9399. doi: 10.1021/jacs.5b04792
6. [6]
  G. Zhan, M.L. Shi, Q. He, et al., Angew. Chem. Int. Ed. 55(2016) 2147-2151. doi: 10.1002/anie.201510825
7. [7]
  M. Montesinos-Magraner, C. Vila, R. Canton, et al., Angew. Chem. Int. Ed. 54(2015) 6320-6324. doi: 10.1002/anie.201501273
8. [8]
  F. Xue, X. Bao, L. Zou, J. Qu, B. Wang, Adv. Synth. Catal. 358(2016) 3971-3976. doi: 10.1002/adsc.201601070
9. [9]
  S. Itsuno, M.M. Hassan, RSC Adv. 4(2014) 52023-52043. doi: 10.1039/C4RA09561H
10. [10]
  W.S. Zhao, Y.L. Zhang, C.K. Qu, et al., Catal. Lett. 144(2014) 1681-1688. doi: 10.1007/s10562-014-1322-5
11. [11]
  C.B. Li, X.M. Shu, L. Li, et al., Chem. Asian J. 11(2016) 2072-2077. doi: 10.1002/asia.v11.14
12. [12]
  I. Billault, R. Launez, M.C. Scherrmann, RSC Adv. 5(2015) 29386-29390. doi: 10.1039/C5RA02292D
13. [13]
  X.M. Xu, T.Y. Cheng, X.C. Liu, et al., ACS Catal. 4(2014) 2137-2142. doi: 10.1021/cs5002459
14. [14]
  D. Cancogni, A. Mandoli, R.P. Jumde, D. Pini, Eur. J. Org. Chem. (2012) 1336-1345.
15. [15]
  Y.Y. Qin, G.X. Yang, L.L. Yang, J. Li, Y.C. Cui, Catal. Lett. 141(2011) 481-488. doi: 10.1007/s10562-010-0509-7
16. [16]
  R. Porta, M. Benaglia, F. Coccia, F. Cozzi, A. Puglisi, Adv. Synth. Catal. 357(2015) 377-383. doi: 10.1002/adsc.201400821
17. [17]
  J. Izquierdo, C. Ayats, A.H. Henselera, M.A. Pericas, Org. Biomol. Chem.13(2015) 4204-4209. doi: 10.1039/C5OB00325C
18. [18]
  J.Q. Zhou, J.W. Wan, X.B. Ma, W. Wang, Org. Biomol. Chem. 10(2012) 4179-4185. doi: 10.1039/c2ob25106j
19. [19]
  G. Kardos, T. Soos, Eur. J. Org. Chem. (2013) 4490-4494.
20. [20]
  R.P. Jumde, A.D. Pietro, A. Manariti, A. Mandoli, Chem. Asian J. 10(2015) 397-404. doi: 10.1002/asia.v10.2
21. [21]
  R.P. Jumde, A. Mandoli, F. De Lorenzi, D. Pini, P. Salvadori, Adv. Synth. Catal. 352(2010) 1434-1440. doi: 10.1002/adsc.v352:9
22. [22]
  R. Mrowczynski, A. Nanb, J. Liebscher, RSC Adv. 4(2014) 5927-5952. doi: 10.1039/c3ra46984k
23. [23]
  R. Dalpozzo, Green Chem. 17(2015) 3671-3686. doi: 10.1039/C5GC00386E
24. [24]
  V. Angamuthu, D.F. Tai, Appl. Catal. A:Gen. 506(2015) 254-260. doi: 10.1016/j.apcata.2015.09.006
25. [25]
  R.B.N. Baiga, M.N. Nadagoudab, R.S. Varma, Coord. Chem. Rev. 287(2015) 137-156. doi: 10.1016/j.ccr.2014.12.017
26. [26]
  O. Gleeson, G.L. Davies, A. Peschiulli, et al., Org. Biomol. Chem. 9(2011) 7929-7940. doi: 10.1039/c1ob06110k
27. [27]
  X.X. Jiang, H. Zhu, X.M. Shi, et al., Adv. Synth. Catal. 355(2013) 308-314.
28. [28]
  J.W. Wan, L. Ding, T. Wu, X.B. Ma, Q. Tang, RSC Adv. 4(2014) 38323-38333. doi: 10.1039/C4RA04720F
29. [29]
  K. Rad-Moghadam, N. Dehghan, J. Mol. Catal. A:Chem. 392(2014) 97-104. doi: 10.1016/j.molcata.2014.05.005
30. [30]
  Y. Lu, Y.D. Yin, B.T. Mayers, Y.N. Xia, Nano Lett. 2(2002) 183-186. doi: 10.1021/nl015681q
31. [31]
  A.K. Tucker-Schwartz, R.A. Farrell, R.L. Garrell, J. Am. Chem. Soc. 133(2011) 11026-11029. doi: 10.1021/ja202292q
32. [32]
  P. Pelmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
33. [33]
  G. Bartoli, M. Bosco, A. Carlone, et al., Angew. Chem. 118(2006) 5088-5092. doi: 10.1002/(ISSN)1521-3757
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