Chinese Journal of Organic Chemistry >
Chiral Borane-Catalyzed Enantioselective Reactions
Received date: 2022-08-15
Revised date: 2022-10-13
Online published: 2022-10-14
Supported by
National Natural Science Foundation of China(2193103)
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.
Key words： chiral borane; enantioselective reaction; hydrogenation; hydrosilylation
Xin Li , Qiuling Song . Chiral Borane-Catalyzed Enantioselective Reactions[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3143 -3151 . DOI: 10.6023/cjoc202208018
| [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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