Citation: Lan Jin, Xie Zongbo, Yang Jiangnan, Meng Jia, Liu Yishuai, Le Zhanggao. One-Pot Multi-component Synthesis of N, O-Acetal Compounds Catalyzed by D-Proline at Room Temperature[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1331-1336. doi: 10.6023/cjoc201911010 shu

One-Pot Multi-component Synthesis of N, O-Acetal Compounds Catalyzed by D-Proline at Room Temperature

Department of Applied Chemistry, East China University of Technology, Nanchang 330013

Corresponding author: Xie Zongbo, zbxie@ecut.edu.cn Le Zhanggao, zhgle@ecit.cn
Received Date: 6 November 2019
Revised Date: 19 December 2019
Available Online: 21 January 2020
Fund Project: the Science and Technology Foundation of Jiangxi Provincial Department of Education KJLD14050the Science and Technology Foundation of Jiangxi Provincial Department of Education GJJ150584the Science and Technology Projects of Jiangxi Province 20161BCB24006Project supported by the National Natural Science Foundation of China (Nos. 21462001, 11765002), the Science and Technology Projects of Jiangxi Province (No. 20161BCB24006), and the Science and Technology Foundation of Jiangxi Provincial Department of Education (Nos. KJLD14050, GJJ150584)the National Natural Science Foundation of China 21462001the National Natural Science Foundation of China 11765002

Figures(4)

In this paper, a convenient method for multi-component one-pot synthesis of N, O-acetal compounds was developed, using aromatic aldehyde, urea and alcohol as materials, alcohol also as solvent and D-proline as catalyst. A series of N, O-acetal compounds were synthesized in good yields after reacting for 30 h at room temperature.
- D-proline,
- N, O-acetal compounds,
- one-pot synthesis,
- room temperature
1. [1]
  Li, G.; Fronczek, F. R.; Antilla, J. C. J. Am. Chem. Soc. 2008, 130, 12216. doi: 10.1021/ja8033334
2. [2]
  Tanaka, J. I.; Higa, T. Tetrahedron Lett. 1996, 37, 5535. doi: 10.1016/0040-4039(96)01149-5
3. [3]
  Jiang, X.; Williams, N.; De Brabander, J. K. Org. Lett. 2007, 9, 227. doi: 10.1021/ol062656o
4. [4]
  Chen, G.; Patanapongpibul, M.; Jiang, Z.; Zhang, Q.; Zheng, S.; Wang, G.; White, J. D.; Chen, Q. H. Org. Biomol. Chem. 2019, 17, 3830. doi: 10.1039/C9OB00556K
5. [5]
  Mosey, R. A.; Floreancig, P. E. Nat. Prod. Rep. 2012, 29, 980. doi: 10.1039/c2np20052j
6. [6]
  Li, M.; Luo, B.; Liu, Q.; Hu, Y.; Ganesan, A.; Huang, P.; Wen, S. Org. Lett. 2013, 16, 10.
7. [7]
  Huang, Y. Y.; Cai, C.; Yang, X. ACS Catal. 2016, 6, 5747. doi: 10.1021/acscatal.6b01725
8. [8]
  Downey, C. W.; Lee, A. Y. K.; Goodin, J. R.; Botelho, C. J.; Stith, W. M. Tetrahedron Lett. 2017, 58, 3496. doi: 10.1016/j.tetlet.2017.07.082
9. [9]
  Zhang, Q.; Xu, D.; Yang, J.; He, L.; Zhang, M. Tetrahedron Lett. 2019, 60, 150992. doi: 10.1016/j.tetlet.2019.150992
10. [10]
  Fletcher, J. T.; Christensen, J. A.; Villa, E. M. Tetrahedron Lett. 2017, 58, 4450. doi: 10.1016/j.tetlet.2017.10.023
11. [11]
  Traboni, S.; Bedini, E.; Giordano, M.; Iadonisi, A. Tetrahedron Lett. 2019, 60, 1777. doi: 10.1016/j.tetlet.2019.05.066
12. [12]
  Lillo, V. J.; Mansilla, J.; Saá, J. M. Org. Biomol. Chem. 2018, 16, 4527. doi: 10.1039/C8OB01007B
13. [13]
  Wan S. Y.; Green, M. E.; Park, J. H.; Floreancig, P. E. Org. Lett. 2007, 9, 5385. doi: 10.1021/ol702184n
14. [14]
  Danson, K. J. Y.; Richard, J. A. Tetrahedron Lett. 2014, 55, 2183. doi: 10.1016/j.tetlet.2014.02.045
15. [15]
  Narina, S. V.; Sudalai, A. Tetrahedron Lett. 2006, 47, 6799. doi: 10.1016/j.tetlet.2006.07.065
16. [16]
  Basumatary, G.; Mohanta, R.; Bez, G. Catal. Lett. 2019, 149, 2776. doi: 10.1007/s10562-019-02809-4
17. [17]
  Wu, H.; Liu, H.; Li, J.; Li, X.; Xiao, H. P.; Jiang, J. Synlett 2019, 30, 1241. doi: 10.1055/s-0037-1610713
18. [18]
  Lucas, F. D. C.; Simone, C. S.; Matheus, V. M.; Paloma, S. P.; Alberto, W. J.; Diogo, M. V.; José Augusto, F. P. V. J. Braz. Chem. Soc. 2018, 30, 893.
19. [19]
  Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600. doi: 10.1039/b923537j
20. [20]
  Bhattacharjee, D.; Sutradhar, D.; Chandra, A. K.; Myrboh, B. Tetrahedron 2017, 73, 3497. doi: 10.1016/j.tet.2017.05.025
21. [21]
  König, S.; Marco, H.; Gäde, G. Amino Acids 2017, 50, 359.
22. [22]
  Allen, W. D.; Czinki, E.; Csaszar, A. G. Chem.-Eur. J. 2004, 10, 4512. doi: 10.1002/chem.200400112
23. [23]
  Usui, I.; Schmidt, S.; Breit, B. Org. Lett. 2009, 11, 1453. doi: 10.1021/ol9001812
24. [24]
  Morales, S.; Guijarro, F. G.; García Ruano, J. L.; Cid, M. B. J. Am. Chem. Soc. 2014, 136, 1082. doi: 10.1021/ja4111418
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