综述与进展

手性硼烷催化的对映选择性反应

  • 李鑫 ,
  • 宋秋玲
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  • 华侨大学新一代物质转化研究所 福建厦门 361021

收稿日期: 2022-08-15

  修回日期: 2022-10-13

  网络出版日期: 2022-10-14

基金资助

国家自然科学基金(2193103)

Chiral Borane-Catalyzed Enantioselective Reactions

  • Xin Li ,
  • Qiuling Song
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  • Institute of Next Generation Matter Transformation, Huaqiao University, Xiamen, Fujian 361021
* Corresponding author. E-mail:

Received date: 2022-08-15

  Revised date: 2022-10-13

  Online published: 2022-10-14

Supported by

National Natural Science Foundation of China(2193103)

摘要

在过去的20年, 手性硼烷已发展成为一种优势催化剂并应用于不对称反应, 一系列结构丰富多样的手性骨架也被应用于手性硼烷的设计与合成中. 与手性过渡金属催化剂相比, 手性硼烷通常需要更少的催化剂用量, 更易于制备, 而且有时还能展现出更好的催化能力, 或给出与过渡金属互补的催化效果. 因此, 手性硼烷催化剂在不对称反应中具有很大的应用价值. 按照反应类型将其分为三大类, 总结和讨论手性硼烷催化的不对称反应.

本文引用格式

李鑫 , 宋秋玲 . 手性硼烷催化的对映选择性反应[J]. 有机化学, 2022 , 42(10) : 3143 -3151 . DOI: 10.6023/cjoc202208018

Abstract

During the past two decades, chiral boranes have emerged as one class of privileged catalysts in asymmetric reactions. A variety of chiral frameworks have been applied in the design and synthesis of chiral borane catalysts. In contrast to chiral transition metal catalysts, chiral boranes generally require lower catalyst loading and are easier to access. Sometimes they exhibit better performance than transition metal catalysts, or give complementary effects in some cases. Accordingly, this catalyst family is of great value in asymmetric reactions. The chiral borane-catalyzed enantioselective reactions are summarized and discussed, which are organized into three parts according to the reaction categories.

参考文献

[1]
Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
[2]
Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
[3]
Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46.
[4]
Stephan, D. W. J. Am. Chem. Soc. 2015, 137, 10018.
[5]
Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124.
[6]
Chen, D.; Klankermayer, J. Chem. Commun. 2008, 2130.
[7]
Chen, D.; Wang, Y.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475.
[8]
Ghattas, G.; Chen, D.; Pan, F.; Klankermayer, J. Dalton Trans. 2012, 41, 9026.
[9]
Sumerin, V.; Chernichenko, K.; Nieger, M.; Leskelä, M.; Rieger, B.; Repo, T. Adv. Synth. Catal. 2011, 353, 2093.
[10]
Lindqvist, M.; Borre, K.; Axenov, K.; Kótai, B.; Nieger, M.; Leskelä, M.; Pápai, I.; Repo, T. J. Am. Chem. Soc. 2015, 137, 4038.
[11]
Liu, Y.; Du, H. J. Am. Chem. Soc. 2013, 135, 6810.
[12]
Wei, S.; Feng, X.; Du, H. Org. Biomol. Chem. 2016, 14, 8026.
[13]
Wang, W.; Feng, X.; Du, H. Org. Biomol. Chem. 2016, 14, 6683.
[14]
Zhang, Z.; Du, H. Angew. Chem., Int. Ed. 2015, 54, 623.
[15]
Zhang, Z.; Du, H. Org. Lett. 2015, 17, 2816.
[16]
Zhang, Z.; Du, H. Org. Lett. 2015, 17, 6266.
[17]
Wei, S.; Du, H. J. Am. Chem. Soc. 2014, 136, 12261.
[18]
Ren, X.; Li, G.; Wei, S.; Du, H. Org. Lett. 2015, 17, 990.
[19]
Liu, X.; Liu, T.; Meng, W.; Du, H. Org. Biomol. Chem. 2018, 16, 8686.
[20]
Lam, J.; Günther, B. A. R.; Farrell, J. M.; Eisenberger, P.; Bestvater, B. P.; Newman, P. D.; Melen, R. L.; Crudden, C. M.; Stephan, D. W. Dalton Trans. 2016, 45, 15303.
[21]
Mercea, D. M.; Howlett, M. G.; Piascik, A. D.; Scott, D. J.; Steven, A.; Fuchter, M. J. Chem. Commun. 2019, 55, 7077.
[22]
Wang, X.; Kehr, G.; Daniliuc, C. G.; Erker, G. J. Am. Chem. Soc. 2014, 136, 3293.
[23]
Ye, K.-Y.; Wang, X.; Daniliuc, C. G.; Kehr, G.; Erker, G. Eur. J. Inorg. Chem. 2017, 368.
[24]
Tu, X.-S.; Zeng, N.-N.; Li, R.-Y.; Zhao, Y.-Q.; Xie, D.-Z.; Peng, Q.; Wang, X.-C. Angew. Chem., Int. Ed. 2018, 57, 15096.
[25]
For a short review on the synthesis and applications of 14 and 15, see: Yang, Z.-Y.; Zhang, M.; Wang, X.-C. Synthesis 2022, 54, 1527.
[26]
Li, X.; Tian, J.-J.; Liu, N.; Tu, X.-S.; Zeng, N.-N.; Wang, X.-C. Angew. Chem., Int. Ed. 2019, 58, 4664.
[27]
Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440.
[28]
Mewald, M.; Fröhlich, R.; Oestreich, M. Chem.-Eur. J. 2011, 17, 9406.
[29]
Mewald, M.; Oestreich, M. Chem.-Eur. J. 2012, 18, 14079.
[30]
Chen, D.; Leich, V.; Pan, F.; Klankermayer, J. Chem.-Eur. J. 2012, 18, 5184.
[31]
Zhu, X.; Du, H. Org. Biomol. Chem. 2015, 13, 1013.
[32]
Süsse, L.; Hermeke, J.; Oestreich, M. J. Am. Chem. Soc. 2016, 138, 6940.
[33]
Liu, X.; Wang, Q.; Han, C.; Feng, X.; Du, H. Chin. J. Chem. 2019, 37, 663.
[34]
Wang, Q.; Han, C.; Feng, X.; Du, H. Chin. J. Org. Chem. 2019, 39, 2257. (in Chinese).
[34]
(王桥天, 韩彩芳, 冯向青, 杜海峰, 有机化学, 2019, 39, 2257.)
[35]
Ren, X.; Du, H. J. Am. Chem. Soc. 2016, 138, 810.
[36]
Ren, X.; Han, C.; Feng, X.; Du, H. Synlett 2017, 28, 2421.
[37]
Morrison, D. J.; Piers, W. E.; Parvez, M. Synlett 2004, 2429.
[38]
Wang, Q.; Chen, J.; Feng, X.; Du, H. Org. Biomol. Chem. 2018, 16, 1448.
[39]
Tian, J.-J.; Yang, Z.-Y.; Liang, X.-S.; Liu, N.; Hu, C.-Y.; Tu, X.-S.; Li, X.; Wang, X.-C. Angew. Chem., Int. Ed. 2020, 59, 18452.
[40]
Tian, J.-J.; Liu, N.; Liu, Q.-F.; Sun, W.; Wang, X.-C. J. Am. Chem. Soc. 2021, 143, 3054.
[41]
Han, C.; Feng, X.; Du, H. Org. Lett. 2021, 23, 7325.
[42]
Zhang, M.; Wang, X.-C. Angew. Chem., Int. Ed. 2021, 60, 17185.
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