Citation: Liu Xiaojian, Chen Pinhong, Wu Fanhong. Application of Oxazoline Ligands in Palladium-Catalyzed Asymmetric Oxidative Functionalization of Alkenes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1797-1804. doi: 10.6023/cjoc201603010 shu

Application of Oxazoline Ligands in Palladium-Catalyzed Asymmetric Oxidative Functionalization of Alkenes

Liu Xiaojian ^a ,
Chen Pinhong ^b,*,, ,
Wu Fanhong ^a,*,,

a.
School of Chemical and Enviromental Engineering, Shanghai Institute of Technology, Shanghai 201418
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Chen Pinhong, pinhongchen@sioc.ac.cn Wu Fanhong, wfh@sit.edu.cn
Received Date: 8 March 2016
Revised Date: 22 April 2016

Fund Project: Project supported by the National Natural Science Foundation of China No. 21472217

Figures(7)

Palladium-catalyzed oxidative functionalization of alkenes is one of the most powerful tools to synthesize complicated molecules. The related asymmetric reactions have received much attention. Due to the oxidative condition, however, compatible chiral ligand is quite limited. Recently, oxazoline-type ligand was applied in these reactions and exhibited good to excellent enantioselectivity. In this review, the recent studies on palladium-catalyzed asymmetric oxidative functionalization of alkenes with oxazoline ligands were summarized.
- oxazoline,
- palladium,
- alkenes,
- asymmetric catalysis
1. [1]
2. [2]
  Minatti, A.; Muñiz, K. Chem. Soc. Rev. 2007, 36, 1142.(b) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981.(c) Mann, S. E.; Benhamou, L.; Sheppard, T. D. Synthesis 2015, 47, 3079.
3. [3]
  Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412.(b) Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824.(c) Chen, P.; Liu, G.; Engle, K. M.; Yu, J.-Q. In Science of Synthesis: Organometallic Complexes of Palladium, Vol. 1, Ed.: Stoltz, B. M., Thieme, Stuttgart, 2013, p. 63.
4. [4]
5. [5]
  Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063.(b) Uozumi, Y.; Kato, K.; Hayashi, T. J. Org. Chem. 1998, 63, 5071.(c) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620.
6. [6]
  Hayashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036.
7. [7]
  Wang, F.; Zhang, Y. J.; Yang, G.; Zhang, W. Tetrahedron Lett. 2007, 48, 4179.
8. [8]
  Wang, F.; Zhang, Y. J.; Wei, H.; Zhang, J.; Zhang, W. Tetrahedron Lett. 2007, 48, 4083.
9. [9]
  Zhang, Y. J.; Wang, F.; Zhang, W. J. Org, Chem. 2007, 72, 9208. (b) Liu, Q.; Wen, K.; Zhang, Z.; Wu, Z.; Zhang, Y. J.; Zhang, W. Tetrahedron 2012, 68, 5209.
10. [10]
  Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem. Int. Ed. 2005, 44, 257.(b) Tietze, L. F.; Stecker, F.; Zinngrebe, J.; Sommer, K. M. Chem. Eur. J. 2006, 12, 8770.
11. [11]
  Tietze, L. F.; Spiegl, D. A.; Stecker, F.; Major, J.; Raith, C.; Große, C. Chem.-Eur. J. 2008, 14, 8956.
12. [12]
  Kawamura, Y.; Kawano, Y.; Matsuda, T.; Ishitobi, Y.; Hosokawa, T. J. Org. Chem. 2009, 74, 3048.
13. [13]
  Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 3076.
14. [14]
  Jensen, K. H.; Webb, J. D.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 17471.
15. [15]
  Jensen, K. H.; Pathak, T. P.; Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2009, 131, 17074.
16. [16]
  Pathak, T. P.; Gligorich, K. M.; Welm, B. M.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 7870.
17. [17]
  Jiang, F.; Wu, Z.; Zhang, W. Tetrahedron Lett. 2010, 51, 5124.
18. [18]
  Yang, G.; Shen, C.; Zhang, W. Angew. Chem., Int. Ed. 2012, 51, 9141.
19. [19]
  Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130.
20. [20]
  He, W.; Yip, K.-T.; Zhu, N.-Y.; Yang, D. Org. Lett. 2009, 11, 5626.
21. [21]
  McDonald, R. I.; White, P. B.; Weinstein, A. B.; Tam. C. P.; Stahl, S. S. Org. Lett. 2011, 13, 2830.
22. [22]
  Koóš, P.; Špánik, I.; Gracza, T. Tetrahedron: Asymmetry 2009, 20, 2720.
23. [23]
  Jana, R.; Pathak, T. P.; Jensen, K. H.; Sigman, M. S. Org. Lett. 2012, 14, 4074.
24. [24]
25. [25]
  Akiyama, K.; Wakabayashi, K.; Mikami, K. Adv. Synth. Catal. 2005, 347, 1569.
26. [26]
  Penn, L.; Shpruhman, A.; Gelman, D. J. Org. Chem. 2007, 72, 3875.
27. [27]
  Yoo, K. S.; Park, C. P.; Yoon, C. H.; Sakaguchi, S.; O'Neill, J.; Jung, K. W. Org. Lett. 2007, 9, 3933.
28. [28]
  Werner, E. W.; Mei, T.-S.; Burckle, A. J.; Sigman, M. S. Science 2012, 338, 1455.(b) Patel, H. H.; Sigman, M. S. J. Am. Chem. Soc. 2015, 137, 3462.
29. [29]
  Mei, T.-S.; Werner, E. W.; Burckle, A. J.; Sigman, M. S. J. Am. Chem. Soc. 2013, 135, 6830.
30. [30]
  Dang, Y.; Qu, S.; Wang, Z.-Y.; Wang, X. J. Am. Chem. Soc. 2014, 136, 986.(b) Xu, L.; Hilton, M. J.; Zhang, X.; Norrby, P.-O.; Wu, Y.-D.; Sigman, M. S.; Wiest, O. J. Am. Chem. Soc. 2014, 136, 1960.
31. [31]
  Mei, T.-S.; Patel, H. H.; Sigman, M. S. Nature 2014, 508, 340.
32. [32]
  Zhang, C.; Santiago, C. B.; Kou, L.; Sigman, M. S. J. Am. Chem. Soc. 2015, 137, 7209.
33. [33]
  Zhang, C.; Santiago, C. B.; Crawford, J. M.; Sigman, M. S. J. Am. Chem. Soc. 2015, 137, 15668.
34. [34]
  Dai, H.; Lu, X. Org. Lett. 2007, 9, 3077.(b) Lin, S.; Lu, X. Org. Lett. 2010, 12, 2536.
35. [35]
  Kikushima, K.; Holder, J. C.; Gatti, M.; Stoltz, B. M. J. Am. Chem. Soc. 2011, 133, 6902.
36. [36]
  He, Q.; Xie, F.; Fu, G.; Quan, M.; Shen, C.; Yang, G.; Gridnev, I. D.; Zhang, W. Org. Lett. 2015, 17, 2250.
37. [37]
  Ingalls, E. L.; Sibbald, P. A.; Kaminsky, W.; Michael, F. E. J. Am. Chem. Soc. 2013, 135, 8854.
38. [38]
  Talbot, E. P. A.; Fernandes, T. A.; McKenna, J. M.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 4101.
39. [39]
  He, Y.; Yang, Z.; Thornbury, R. T.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 12207.
40. [40]
  Yu, F.; Chen, P.; Liu, G. Org. Chem. Front. 2015, 2, 819.
41. [41]
  Xu, T.; Qiu, S.; Liu, G. J. Organomet. Chem. 2011, 696, 46.
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