REVIEW

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

  • Liu Xiaojian ,
  • Chen Pinhong ,
  • Wu Fanhong
Expand
  • 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

Received date: 2016-03-08

  Revised date: 2016-04-22

  Online published: 2016-05-03

Supported by

Project supported by the National Natural Science Foundation of China (No. 21472217).

Abstract

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.

Cite this article

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

References

[1] (a) Smidt, J.; Hafner, W.; Jira, R.; Sedlmeier, J.; Sieber, R.; Rüttinger, R.; Kojer, H. Angew. Chem. 1959, 71, 176.
(b) Smidt, J.; Hafner, W.; Jira, R.; Sieber, R.; Sedlmeier, J.; Sabel, A. Angew. Chem., Int. Ed. 1962, 1, 80.
(c) Jira, R. Angew. Chem., Int. Ed. 2009, 48, 9034.
[2] (a) 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] (a) 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] (a) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
(b) O'Reilly, S.; Guiry, P. J. Synthesis 2014, 46, 722.
(c) Liu, L.; Ma, H.; Wu, Y.; Yuan, D.; Liu, J.; Fu, B.; Ma, X. Chin. J. Org. Chem. 2013, 33, 2283 (in Chinese).
(刘磊, 麻红利, 吴燕华, 袁德凯, 刘吉平, 傅滨, 马晓东, 有机化学, 2013, 33, 2283.)
[5] (a) 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] Hayashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036.
[7] Wang, F.; Zhang, Y. J.; Yang, G.; Zhang, W. Tetrahedron Lett. 2007, 48, 4179.
[8] Wang, F.; Zhang, Y. J.; Wei, H.; Zhang, J.; Zhang, W. Tetrahedron Lett. 2007, 48, 4083.
[9] (a) 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] (a) 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] Tietze, L. F.; Spiegl, D. A.; Stecker, F.; Major, J.; Raith, C.; Große, C. Chem.-Eur. J. 2008, 14, 8956.
[12] Kawamura, Y.; Kawano, Y.; Matsuda, T.; Ishitobi, Y.; Hosokawa, T. J. Org. Chem. 2009, 74, 3048.
[13] Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 3076.
[14] Jensen, K. H.; Webb, J. D.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 17471.
[15] Jensen, K. H.; Pathak, T. P.; Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2009, 131, 17074.
[16] Pathak, T. P.; Gligorich, K. M.; Welm, B. M.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 7870.
[17] Jiang, F.; Wu, Z.; Zhang, W. Tetrahedron Lett. 2010, 51, 5124.
[18] Yang, G.; Shen, C.; Zhang, W. Angew. Chem., Int. Ed. 2012, 51, 9141.
[19] Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130.
[20] He, W.; Yip, K.-T.; Zhu, N.-Y.; Yang, D. Org. Lett. 2009, 11, 5626.
[21] McDonald, R. I.; White, P. B.; Weinstein, A. B.; Tam. C. P.; Stahl, S. S. Org. Lett. 2011, 13, 2830.
[22] Koóš, P.; Špánik, I.; Gracza, T. Tetrahedron: Asymmetry 2009, 20, 2720.
[23] Jana, R.; Pathak, T. P.; Jensen, K. H.; Sigman, M. S. Org. Lett. 2012, 14, 4074.
[24] (a) Karimi, B.; Behzadnia, H.; Elhamifar, D.; Akhavan, P. F.; Esfahani, F. K.; Zamani, A. Synthesis 2010, 1399.
(b) Li, H.; Ding, C.; Xu, B.; Hou, X. Acta Chim. Sinica 2014, 72, 765 (in Chinese).
(李浩, 丁昌华, 许斌, 侯雪龙, 化学学报, 2014, 72, 765.)
(c) Shang, X.; Liu, Z. Chin. J. Org. Chem. 2015, 35, 522 (in Chinese).
(尚筱洁, 柳忠全, 有机化学, 2015, 35, 522.)
[25] Akiyama, K.; Wakabayashi, K.; Mikami, K. Adv. Synth. Catal. 2005, 347, 1569.
[26] Penn, L.; Shpruhman, A.; Gelman, D. J. Org. Chem. 2007, 72, 3875.
[27] Yoo, K. S.; Park, C. P.; Yoon, C. H.; Sakaguchi, S.; O'Neill, J.; Jung, K. W. Org. Lett. 2007, 9, 3933.
[28] (a) 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] Mei, T.-S.; Werner, E. W.; Burckle, A. J.; Sigman, M. S. J. Am. Chem. Soc. 2013, 135, 6830.
[30] (a) 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] Mei, T.-S.; Patel, H. H.; Sigman, M. S. Nature 2014, 508, 340.
[32] Zhang, C.; Santiago, C. B.; Kou, L.; Sigman, M. S. J. Am. Chem. Soc. 2015, 137, 7209.
[33] Zhang, C.; Santiago, C. B.; Crawford, J. M.; Sigman, M. S. J. Am. Chem. Soc. 2015, 137, 15668.
[34] (a) Dai, H.; Lu, X. Org. Lett. 2007, 9, 3077.
(b) Lin, S.; Lu, X. Org. Lett. 2010, 12, 2536.
[35] Kikushima, K.; Holder, J. C.; Gatti, M.; Stoltz, B. M. J. Am. Chem. Soc. 2011, 133, 6902.
[36] He, Q.; Xie, F.; Fu, G.; Quan, M.; Shen, C.; Yang, G.; Gridnev, I. D.; Zhang, W. Org. Lett. 2015, 17, 2250.
[37] Ingalls, E. L.; Sibbald, P. A.; Kaminsky, W.; Michael, F. E. J. Am. Chem. Soc. 2013, 135, 8854.
[38] Talbot, E. P. A.; Fernandes, T. A.; McKenna, J. M.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 4101.
[39] He, Y.; Yang, Z.; Thornbury, R. T.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 12207.
[40] Yu, F.; Chen, P.; Liu, G. Org. Chem. Front. 2015, 2, 819.
[41] Xu, T.; Qiu, S.; Liu, G. J. Organomet. Chem. 2011, 696, 46.

Outlines

/