Citation: Yan Wang, Lanying Wang, Xiangdong Hu, YunXia Wang. 缩醛/缩酮的合成研究进展[J]. University Chemistry, ;2022, 37(1): 210402. doi: 10.3866/PKU.DXHX202104026 shu

缩醛/缩酮的合成研究进展

National Experimental Teaching Demonstration Center of Chemistry, School of Chemistry and Materials Science, Northwestern University, Xi'an 710127, China

Received Date: 12 April 2021

醛/酮与醇或原甲酸酯进行亲核加成反应生成的产物缩醛/缩酮，是一类重要的有机化合物。在有机合成中，该反应也广泛用于醛/酮羰基的保护或者乙二醇的保护，因此，缩醛/缩酮的合成研究引起广泛的关注。本文根据反应体系的不同，从酸催化、电催化和光催化三个方面对近年来缩醛/缩酮的合成研究进展进行详细综述。期望该综述作为学生基础有机化学课程的课后拓展阅读内容，能加深学生对基础反应的理解，培养学生的科研创新思维。
- Aldehyde/ketone,
- Synthesis,
- Acetal/ketal
1. [1]
  Greene, T. W.; Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons, Inc.:New Jersey, USA, 2007; pp. 424-428.
2. [2]
  Bio, M. M.; Hansen, K. B.; Gipson, J. Org. Process Res. Dev. 2008, 12 (5), 892.
3. [3]
  Maarse, H. Volatile Compounds I Foods and Beverages; Marcel Dekker, Inc.:New York, USA, 1991.
4. [4]
  Silva, P. H. R.; Gonçalves, V. L. C.; Mota, C. J. A. Bioresour. Technol. 2010, 101 (15), 6225.
5. [5]
  Shimizu, K.; Hayashi, E.; Hatamachi, T.; Kodama, T.; Kitayama, Y. Tetrahedron Lett. 2004, 45 (26), 5135.
6. [6]
  Dong, J. L.; Yu, L. S. H.; Xie, J. W. ACS Omega 2018, 3 (5), 4974.
7. [7]
  Clerici, A.; Pastori, N.; Porta, O. Tetrahedron 1998, 54 (51), 15679.
8. [8]
  Firouzabadi, H; Iranpoor, N.; Karimi, B. Synlett 1999, 3, 321.
9. [9]
  Qi, J. Y.; Ji, J. X.; Yueng, C. H. Kwong, H. L.; Chan, A. S. C. Tetrahedron Lett. 2004, 45 (41), 7719.
10. [10]
  Ranu, B. C.; Jana, R.; Samanta, S. Adv. Synth. Catal. 2004, 346 (4), 446.
11. [11]
  Velusamy, S.; Punniyamurthy, T. Tetrahedron Lett. 2004, 45 (25), 4917.
12. [12]
  da Silva, M. J.; Teixiera, M. G.; Natalino, R. New J. Chem. 2019, 43 (22), 8606.
13. [13]
  Lee, S. H.; Lee, J. H.; Yoon, C. M. Tetrahedron Lett. 2002, 43 (15), 2699.
14. [14]
  Leonard, N. M.; Oswald, M. C.; Freiberg, D. A.; Nattier, B. A.; Smith, R. C.; Mohan, R. S. J. Org. Chem. 2002, 67 (150), 5202.
15. [15]
  Smith, B. M.; Graham, A. E. Tetrahedron Lett. 2006, 47 (52), 9317.
16. [16]
  Williams, D. B. G.; Lawton, M. C. Green Chem. 2008, 10 (9), 914.
17. [17]
  Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46 (48), 8319.
18. [18]
  Lyons, D. J. M.; Crocker, R. D.; Enders, D.; Nguyen, T. V. Green Chem. 2017, 19 (17), 3993.
19. [19]
  Procuranti, B.; Connon, S. J. Org. Lett. 2008, 10 (21), 4935.
20. [20]
  Myles, L.; Gore, R.; Spulak, M.; Gathergood, N.; Connon, S. J. Green Chem. 2010, 12 (7), 1157.
21. [21]
  Zhu, Y. W.; Shi, Y. X.; Wu, Z. H. Chem. Lett. 2016, 45 (12), 1428.
22. [22]
  Mensah, E. A.; Green, S. D.; West, J.; Kindoll, T.; Lazaro-Martinez, B. Synlett 2019, 30 (15), 1810.
23. [23]
  Subaramanian, M.; Landge, V. G.; Mondal, A.; Gupta, V.; Balaraman, E. Chem. Asian J. 2019, 14 (24), 4557.
24. [24]
  Karimi, B.; Ashtiani, A. M. Chem. Lett. 1999, 28 (11), 1199.
25. [25]
  Karimi, B.; Seradj, H.; Ebrahimian, G. R. Synlett 1999, 9, 1456.
26. [26]
  Karimi, B.; Hazarkhani, H.; Maleki, J. Synthesis 2005, 2, 279.
27. [27]
  Karimi, B.; Golshani, B. Synthesis 2002, 6, 784.
28. [28]
  Liu, C. Y.; Shen, Y. L.; Xiao, Z. H.; Yang, H.; Han, X.; Yuan, K. D.; Ding, Y. Green Chem. 2019, 21 (15), 4030.
29. [29]
  Hong, Y.; Niu, L. B.; Wang, S. C.; Liu, T. Y.; Singh, A. K.; Lei, A. W. Org. Lett. 2017, 19 (1), 122.
30. [30]
  Nikitas, F. N.; Triandafillidi, I.; Kokotos, C. G. Green Chem. 2019, 21 (3), 669.
31. [31]
  Spiliopoulou, N.; Nikitas, N. F.; Kokotos, C. G. Green Chem. 2020, 22 (11), 3539.
32. [32]
  Yu, L. Y.; Lin, C. Y.; Liao, C. S.; Zeng, X. H.; Chen, X. W.; Zhu, Z. Z.; Huang, Y. B.; Li, Y. B.; Chen, L. Environ. Chem. Lett. 2020, 18 (4), 1353.
33. [33]
  Ye, M. Y.; Zhou, G.; Li, B. X.; Liu, J. H. Sci. Sin. Chim. 2013, 43 (5), 551.
34. [34]
  Khan, M. A.; Teixeira, I. F.; Li, M. M. J.; Koito, Y.; Tsang, S. C. E. Chem. Commun. 2016, 52 (13), 2772.
35. [35]
  Lin, Y. X.; Guo, J.; Martin, J. S.; Han, C.; Martinez, R.; Yan, Y. Chem. Eur. J. 2020, 26 (58), 13118.
36. [36]
  Chen, J.; Cen, J.; Xu, X. L.; Li, X. N. Catal. Sci. Technol. 2016, 6, 349.
37. [37]
  Gu, Q.; Jia, Q. H.; Long, J. L.; Gao, Z. W. ChemCatChem 2019, 11, 669.
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