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2022 , Vol. 42 >Issue 10: 3280 - 3294

DOI: https://doi.org/10.6023/cjoc202206032

综述与进展

经历金属氢物种制备手性叔胺的不对称催化研究进展

  • 范天翔 ,
  • 刘媛媛
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  • 华东师范大学化学与分子工程学院 上海 200241

收稿日期: 2022-05-23

  修回日期: 2022-07-06

  网络出版日期: 2022-08-10

基金资助

国家自然科学基金(21871088)

收起

Recent Advances in Synthesis of Chiral Tertiary Amines via Asymmetric Catalysis Involving Metal-Hydride Species

  • Tianxiang Fan ,
  • Yuanyuan Liu
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  • School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241
* Corresponding author. E-mail:

Received date: 2022-05-23

  Revised date: 2022-07-06

  Online published: 2022-08-10

Supported by

National Natural Science Foundation of China(21871088)

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摘要

手性叔胺作为一种重要的化合物骨架, 存在于各种药物、天然产物和有机功能材料中, 因而受到合成化学家们的重视. 目前已有几种不同的经历金属氢物种的合成手性叔胺的方法被报道. 根据不同的反应类型, 本文从不对称氢胺化、不对称氢化、不对称还原胺化和“借氢”策略中醇的不对称胺化四个方面对近年来的研究进展进行总结. 同时介绍了各策略中相应反应的机理, 并对该领域的未来发展做了展望.

关键词： 手性叔胺; 不对称催化; 金属氢物种; 氢化; 氢胺化

本文引用格式

范天翔 , 刘媛媛 . 经历金属氢物种制备手性叔胺的不对称催化研究进展[J]. 有机化学, 2022 , 42(10) : 3280 -3294 . DOI: 10.6023/cjoc202206032

Abstract

Chiral tertiary amines, as a class of important skeleton, exist in various drugs, natural products, and organic functional materials. Therefore, the development of efficient synthetic methods for the preparation of chiral tertiary amines has attracted much attention from chemists and become one of the research hotspots in recent years. Until now, several asymmetric catalytic methods involving metal-hydride species have been developed. According to different reaction types, the research progress in recent years is summarized from four aspects: asymmetric hydroamination, asymmetric hydrogenation, asymmetric reductive amination, and asymmetric amination of alcohols via the ‘borrowing hydrogen’ strategy. At the same time, the corresponding reaction mechanism of each strategy is introduced, and the future development of this field is envisioned.

Key words： tertiary amine; asymmetric catalysis; metal-hydride species; hydrogenation; hydroamination

参考文献

[1]
(a) Onyeagusi, C. I.; Malcolmson, S. J. ACS Catal. 2020, 10, 12507.
[1]
(b) Robert-Paganin, J.; Pylypenko, O.; Kikuti, C.; Sweeney, H. L.; Houdusse, A. Chem. Rev. 2020, 120, 5.
[1]
(c) Cai, M.; Xu, K.; Li, Y.; Nie, Z.; Zhang, L.; Luo, S. J. Am. Chem. Soc. 2021, 143, 1078.
[1]
(d) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.
[1]
(e) Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1.
[2]
https://njardarson.lab.arizona.edu/content/top-pharmaceuticals-poster
[3]
(a) Roesky, P. W.; Müller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708.
[3]
(b) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
[3]
(c) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795.
[4]
(a) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016, 116, 14769.
[4]
(b) Barrios-Rivera, J.; Xu, Y.; Wills, M.; Vyas, V. K. Org. Chem. Front. 2020, 7, 3312.
[4]
(c) Fleury, B., N.; Castillón, S.; Claver, C. ChemCatChem 2010, 2, 1346.
[4]
(d) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
[5]
Reshi, N. U. D.; Saptal, V. B.; Beller, M.; Bera, J. K. ACS Catal. 2021, 11, 13809.
[6]
Gomez, S.; Peters, J. A.; Maschmeyer, T. Adv. Synth. Catal. 2002, 344, 1037.
[7]
Wu, Z.; Du, S.; Gao, G.; Yang, W.; Yang, X.; Huang, H.; Chang, M. Chem. Sci. 2019, 10, 4509.
[8]
(a) Swain, S. P.; Shri, O.; Ravichandiran, V. Mol. Catal. 2021, 508, 111576.
[8]
(b) Tang, S.; Li, Z.; Shao, Y.; Sun, J. Org. Lett. 2019, 21, 7228.
[9]
Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 10830.
[10]
Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 15746.
[11]
(a) Jordan, A. J.; Lalic, G.; Sadighi, J. P. Chem. Rev. 2016, 116, 8318.
[11]
(b) Deutsch, C.; Krause, N. Chem. Rev. 2008, 108, 2916.
[12]
Snieckus, V.; Green, J. Synlett 2014, 25, 2258.
[13]
(a) Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 1498.
[13]
(b) Perego, L. A.; Blieck, R.; Groué, A.; Monnier, F.; Taillefer, M.; Ciofini, I.; Grimaud, L. ACS Catal. 2017, 7, 4253.
[14]
Perego, L. A.; Blieck, R.; Michel, J.; Ciofini, I.; Grimaud, L.; Taillefer, M.; Monnier, F. Adv. Synth. Catal. 2017, 359, 4388.
[15]
Niljianskul, N.; Zhu, S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2015, 54, 1638.
[16]
Yang, Y.; Shi, S.-L.; Niu, D.; Liu, P.; Buchwald, S. L. Science 2015, 349, 62.
[17]
Xi, Y.; Butcher, T. W.; Zhang, J.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 776.
[18]
Nishikawa, D.; Hirano, K.; Miura, M. J. Am. Chem. Soc. 2015, 137, 15620.
[19]
Takata, T.; Nishikawa, D.; Hirano, K.; Miura, M. Chem.-Eur. J. 2018, 24, 10975.
[20]
Takata, T.; Hirano, K.; Miura, M. Org. Lett. 2019, 21, 4284.
[21]
Yu, L.; Somfai, P. Angew. Chem., Int. Ed. 2019, 58, 8551.
[22]
Ichikawa, S.; Dai, X.-J.; Buchwald, S. L. Org. Lett. 2019, 21, 4370.
[23]
Ichikawa, S.; Buchwald, S. L. Org. Lett. 2019, 21, 8736.
[24]
Feng, S.; Hao, H.; Liu, P.; Buchwald, S. L. ACS Catal. 2020, 10, 282.
[25]
Yang, Q.; Li, S.; Wang, J. ChemCatChem 2020, 12, 3202.
[26]
Vanable, E. P.; Kennemur, J. L.; Joyce, L. A.; Ruck, R. T.; Schultz, D. M.; Hull, K. L. J. Am. Chem. Soc. 2019, 141, 739.
[27]
Berthold, D.; Breit, B. Org. Lett. 2018, 20, 598.
[28]
Velasco-Rubio, Á.; Bernárdez, R.; Varela, J. A.; Saá, C. J. Org. Chem. 2021, 86, 10889.
[29]
Yang, X.-H.; Dong, V. M. J. Am. Chem. Soc. 2017, 139, 1774.
[30]
Adamson, N. J.; Hull, E.; Malcolmson, S. J. J. Am. Chem. Soc. 2017, 139, 7180.
[31]
Park, S.; Malcolmson, S. J. ACS Catal. 2018, 8, 8468.
[32]
Jiu, A. Y.; Slocumb, H. S.; Yeung, C. S.; Yang, X.-H.; Dong, V. M. Angew. Chem., Int. Ed. 2021, 60, 19660.
[33]
(a) Zhang, Z.; Butt, N. A.; Zhou, M.; Liu, D.; Zhang, W. Chin. J. Chem. 2018, 36, 443.
[33]
(b) Quan, M.; Wu, L.; Yang, G.; Zhang, W. Chem. Commun. 2018, 54, 10394.
[33]
(c) Wu, L.; Yang, G.; Zhang, W. CCS Chem. 2020, 2, 623.
[33]
(d) Clevenger, A. L.; Stolley, R. M.; Aderibigbe, J.; Louie, J., Chem. Rev. 2020, 120, 6124.
[33]
(e) Shi, D.; Wojcieszak, R.; Paul, S.; Marceau, E. Catalysts 2019, 9, 451.
[33]
(f) Mukherjee, A.; Milstein, D. ACS Catal. 2018, 8, 11435.
[34]
Pawlas, J.; Nakao, Y.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 3669.
[35]
Tran, G.; Shao, W.; Mazet, C. J. Am. Chem. Soc. 2019, 141, 14814.
[36]
Long, J.; Wang, P.; Wang, W.; Li, Y.; Yin, G. iScience 2019, 22, 369.
[37]
Abdine, R. A. A.; Hedouin, G.; Colobert, F.; Wencel-Delord, J. ACS Catal. 2021, 11, 215.
[38]
Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
[39]
Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.; Holz, J.; Börner, A. Tetrahedron Lett. 2000, 41, 2351.
[40]
Hou, G.-H.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 11774.
[41]
Hou, G.-H.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. J. Am. Chem. Soc. 2009, 131, 1366.
[42]
Yan, P.-C.; Xie, J.-H.; Hou, G.-H.; Wang, L.-X.; Zhou, Q.-L. Adv. Synth. Catal. 2009, 351, 3243.
[43]
Yan, P.; Xie, J.; Zhou, Q. Chin. J. Chem. 2010, 28, 1736.
[44]
Ji, Y.; Feng, G.-S.; Chen, M.-W.; Shi, L.; Du, H.; Zhou, Y.-G. Org. Chem. Front. 2017, 4, 1125.
[45]
(a) Yasukawa, T.; Masuda, R.; Kobayashi, S. Nat. Catal. 2019, 2, 1088.
[45]
(b) Huang, H.; Wu, Z.; Gao, G.; Zhou, L.; Chang, M. Org. Chem. Front. 2017, 4, 1976.
[45]
(c) Huang, H.; Liu, X.; Zhou, L.; Chang, M.; Zhang, X. Angew. Chem., Int. Ed. 2016, 55, 5309.
[45]
(d) Chang, M.; Liu, S.; Huang, K.; Zhang, X. Org. Lett. 2013, 15, 4354.
[45]
(e) Chi, Y.; Zhou, Y.-G.; Zhang, X. J. Org. Lett. 2003, 68, 4120.
[46]
Jagadeesh, R. V.; Murugesan, K.; Alshammari, A. S.; Neumann, H.; Pohl, M.-M.; Radnik, J.; Beller, M. Science 2017, 358, 326.
[47]
Gilbert, S. H.; Tin, S.; Fuentes, J. A.; Fanjul, T.; Clarke, M. L. Tetrahedron 2021, 80, 131863.
[48]
Chen, Y.; He, Y.-M.; Zhang, S.; Miao, T.; Fan, Q.-H. Angew. Chem., Int. Ed. 2019, 58, 3809.
[49]
Wang, L.-R.; Chang, D.; Feng, Y.; He, Y.-M.; Deng, G.-J.; Fan, Q.-H. Org. Lett. 2020, 22, 2251.
[50]
(a) Liu, Y.; Tao, R.; Lin, Z.-K.; Yang, G.; Zhao, Y. Nat. Commun. 2021, 12, 5035.
[50]
(b) Yang, G.; Pan, J.; Ke, Y.-M.; Liu, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2021, 60, 20689.
[50]
(c) Xi, X.; Li, Y.; Wang, G.; Xu, G.; Shang, L.; Zhang, Y.; Xia, L. Org. Biomol. Chem. 2019, 17, 7651.
[50]
(d) Corma, A.; Navas, J.; Sabater, M. J. Chem. Rev. 2018, 118, 1410.
[50]
(e) Irrgang, T.; Kempe, R. Chem. Rev. 2019, 119, 2524.
[51]
(a) Zhang, Y.; Lim, C.-S.; Sim, D. S. B.; Pan, H.-J.; Zhao, Y. Angew. Chem., Int. Ed. 2014, 53, 1399.
[51]
(b) Lim, C. S.; Quach, T. T.; Zhao, Y. Angew. Chem., Int. Ed. 2017, 56, 7176.
[51]
(c) Yang, P.; Zhang, C.; Ma, Y.; Zhang, C.; Li, A.; Tang, B.; Zhou, J. S. Angew. Chem., Int. Ed. 2017, 56, 14702.
[51]
(d) Xu, G.; Yang, G.; Wang, Y.; Shao, P.-L.; Y.; Xia, L.; Zhao, Y. Angew. Chem., Int. Ed. 2019, 58, 14082.
[51]
(e) Pan, H.-J.; Lin, Y.; Gao, T.; Lau, K. K.; Feng, W.; Yang, B.; Zhao, Y. Angew. Chem., Int. Ed. 2021, 60, 18599.
[51]
(f) Rong, Z.-Q.; Yu, Z.; Weng, C.; Yang, L.-C.; Lu, S.; Lan, Y.; Zhao, Y. ACS Catal. 2020, 10, 9464.
[52]
Fujita, K.-i.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525.
[53]
Miao, L.; DiMaggio, S. C.; Shu, H.; Trudell, M. L. Org. Lett. 2009, 11, 1579.
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