Citation: Zhi Chai, Huashan Huang, Xukai Shi, Yujing Lan, Zhentao Yuan, Hong Yan. Wittig反应的立体选择性[J]. University Chemistry, ;2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046 shu

Wittig反应的立体选择性

Zhi Chai ¹ ,
Huashan Huang ¹ ,
Xukai Shi ² ,
Yujing Lan ¹ ,
Zhentao Yuan ¹ ,
Hong Yan ^1,,

1.
College of Chemistry, Fuzhou University, Fuzhou 350108, China;
2.
Zijin School of Geology and Mining, Fuzhou University, Fuzhou 350108, China

Corresponding author: Hong Yan, hongyan@fzu.edu.cn
Received Date: 15 October 2024
Revised Date: 6 January 2025

Wittig反应是合成烯烃的经典方法，但是国内外有机化学教材中对Wittig反应的机理以及立体选择性只进行了简单介绍。本文介绍了国际上提出的几种Wittig反应机理以及对立体选择性的解释，旨在对教材中Wittig反应的知识进行补充，帮助学生理解Wittig反应机理以及立体选择性，进一步夯实学生的有机化学知识基础。
- Wittig reaction,
- Phosphorus ylide,
- Reaction mechanism,
- Stereoselectivity
1. [1]
  Byrne, P. A.; Gilheany, D. G. Chem. Soc. Rev. 2013, 42, 6670.
2. [2]
3. [3]
4. [4]
  Vollhardt, P.; Schore, N. E. Organic Chemistry Structure and Function, 7th ed.; W. H. Freeman and Company: New York, NY, USA, 2014; p. 769.
5. [5]
  Klein, D. Organic Chemistry; John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2012; p. 950.
6. [6]
  Bruice, P. Y. Organic Chemistry, 8th ed.; Pearson Education, Inc.: Upper Saddle River, NJ, USA, 2015; p. 776.
7. [7]
  Vedejs, E.; Peterson, M. J. Stereochemistry and Mechanism in the Wittig Reaction. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; John Wiley & Sons, Inc.: New York, NY, USA, 1994; p. 46.
8. [8]
  Ayer, W. A.; Lee, S. P.; Tsuneda, A.; Hiratsuka, Y. Can. J. Microbiol. 1980, 69, 636.
9. [9]
  Kirsch, S. F.; Overman, L. E. J. Am. Chem. Soc. 2005, 127, 2866.
10. [10]
  Uchiyama, Y.; Yamagishi, S.; Yasukawa, T. J. Org. Chem. 2022, 87, 15899.
11. [11]
  Farfán, P.; Gómez, S.; Restrepo A. J. Org. Chem. 2019, 84, 14644.
12. [12]
  Robiette, R.; Richardson, J.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2006, 128, 2394.
13. [13]
  Bergelson, L. D.; Shemyakin, M. M. Tetrahedron 1963, 19, 149.
14. [14]
  Bestmann, H. J. Pure Appl. Chem. 1980, 52, 771.
15. [15]
  Vedejs, E.; Fleck, T. J. Am. Chem. Soc. 1989, 111, 5861.
16. [16]
  Bofill, J. M.; Severi, M.; Quapp, W.; Ribas-Ariño, J.; Moreira, I. D. R.; Albareda, G. Chem. Eur. J. 2024, 30, e202400173.
17. [17]
  Schlosser, M.; Schaub, B. J. Am. Chem. Soc. 1982, 104, 5821.
18. [18]
  Schweizer, E. E.; Crouse, D. M.; Minami, T.; Wehman, A. J. Chem. Soc. D: Chem. Commun. 1971, 1000.
19. [19]
  Olah, G. A.; Krishnamurthy, V. V. J. Am. Chem. Soc. 1982, 104, 3987.
20. [20]
  Ward, W. J.; McEwen, W. E. J. Org. Chem. 1990, 55, 493.
21. [21]
  Chamorro, E.; Duque-Noreña, M.; Gutierrez-Sánchez, N.; Rincón, E.; Domingo, L. R. J. Org. Chem. 2020, 85, 6675.
22. [22]
  Adda, A.; Aoul, R. H.; Sediki, H.; Sehailia, M.; Krallafa, A. M. Theor. Chem. Acc. 2023, 142,102.
23. [23]
  López, J. G.; Peraza, P. M. S.; lesias, M. J.; Roces, L.; García-Granda, S.; Ortiz, F. L. J. Org. Chem. 2020, 85, 14570.
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