综述与进展

噁唑啉类配体在钯催化烯烃的不对称氧化官能化反应中的应用

  • 刘小建 ,
  • 陈品红 ,
  • 吴范宏
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  • a 上海应用技术学院化学与环境工程学院 上海 201418;
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032

收稿日期: 2016-03-08

  修回日期: 2016-04-22

  网络出版日期: 2016-05-03

基金资助

国家自然科学基金(No. 21472217)资助项目.

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

  • Liu Xiaojian ,
  • Chen Pinhong ,
  • Wu Fanhong
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  • 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).

摘要

钯催化烯烃的官能化反应是实现简单烯烃向复杂分子转化的高效方法之一,尤其是烯烃的氧化官能化反应,能够更加高效地得到烯烃的双官能化的产物,其不对称反应也受到化学家们的广泛关注. 但是在氧化双官能化反应中,要求手性配体能够耐氧化. 近年来的研究表明,噁唑啉配体在这类反应中是能够兼容的,而且可以得到优秀的对映选择性. 本综述介绍了近期噁唑啉配体在钯催化烯烃的氧化官能化反应中的应用进展.

本文引用格式

刘小建 , 陈品红 , 吴范宏 . 噁唑啉类配体在钯催化烯烃的不对称氧化官能化反应中的应用[J]. 有机化学, 2016 , 36(8) : 1797 -1804 . DOI: 10.6023/cjoc201603010

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.

参考文献

[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.

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