SIOC English
有机化学
高级检索

有机化学 >

0 0

DOI: https://doi.org/10.6023/cjoc202606009

综述与进展

过渡金属催化不对称氢化合成手性内酰胺的研究进展

  • 刘春萌 ,
  • 魏雨晴 ,
  • 袁乾家 ,
  • 毛国梁 ,
  • 张万斌
展开
  • a东北石油大学化学化工学院 黑龙江省聚烯烃新材料重点实验室 大庆 163318;
    b上海交通大学化学化工学院 上海市手性药物分子工程重点实验室 上海 200240

收稿日期: 2026-06-09

  修回日期: 2026-06-23

  网络出版日期: 2026-06-26

收起

Research Progress on the Synthesis of Chiral Lactams via Transition Metal-Catalyzed Asymmetric Hydrogenation

  • Liu Chunmeng ,
  • Wei Yuqing ,
  • Yuan Qianjia ,
  • Mao Guoliang ,
  • Zhang Wanbin
Expand
  • aHeilongjiang Provincial Key Laboratory of Polyolefin New Materials, College of Chemistry & Chemical Engineering Northeast Petroleum University, Daqing, 163318;
    bShanghai Key Laboratory of Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240

Received date: 2026-06-09

  Revised date: 2026-06-23

  Online published: 2026-06-26

Supported by

Project supported by the by the Shanghai Municipal Science and Technology Major Project, Natural Science Foundation of Shanghai (24ZR1439600), the National Key R&D Program of China (No. 2023YFA1506400); Wanbin Zhang is a SANS Scholar.

Fold

摘要

手性内酰胺广泛存在于天然产物与药物分子中,也是一类重要的合成中间体,其高效不对称合成具有重要的研究价值. 过渡金属催化的不对称氢化反应具有原子经济性好、催化效率高及操作简便等优势,是最具工业化潜力的手性合成技术之一. 近年来,基于铱、铑、钌、钯及镍等金属的催化氢化体系相继建立,并成功实现了手性内酰胺的高效不对称合成. 根据金属催化剂的类型进行分类,本文综述了不同催化体系的特点、反应底物适用范围及产物立体选择性来源,并总结了其在药物或天然产物合成中的应用. 最后,对该领域的发展前景进行了展望,以期为手性内酰胺的高效合成提供参考.

关键词： 内酰胺; 不对称氢化; 不对称催化; 过渡金属

本文引用格式

刘春萌 , 魏雨晴 , 袁乾家 , 毛国梁 , 张万斌 . 过渡金属催化不对称氢化合成手性内酰胺的研究进展[J]. 有机化学, 0 : 0 . DOI: 10.6023/cjoc202606009

Abstract

Chiral lactams are widely found in natural products and pharmaceutical molecules, and also serve as important synthetic intermediates. Therefore, the efficient asymmetric construction of chiral lactams is of significant research value. Transition metal-catalyzed asymmetric hydrogenation features atom economy, high catalytic efficiency, and operational simplicity, making it one of the most industrially promising technologies for the synthesis of chiral compounds. In recent years, catalytic asymmetric hydrogenation systems based on transition metals such as iridium, rhodium, ruthenium, palladium, and nickel have been successively developed, enabling the highly efficient synthesis of chiral lactams. Classified according to the transition metal catalyst type, this review summarizes the characteristics of different catalytic systems, including the substrate scope, the origin of stereoselectivity and the mechanism, and the applications in the synthesis of pharmaceuticals and natural products. Finally, the current challenges and future prospects of this field are discussed, with the aim of providing useful guidance for the efficient synthesis of chiral lactams.

Key words： lactams; asymmetric hydrogenation; asymmetric catalysis; transition metal

参考文献

[1] (a) Nay, B.; Riache, N.; Evanno, L. Nat. Prod. Rep. 2009, 26, 1044.
(b) Royer, J., Ed. Asymmetric Synthesis of Nitrogen Heterocycles; Wiley-VCH: Weinheim, 2009.
(c) Bregman, H.; Chakka, N.; Guzman-Perez, A.; Gunaydin, H.; Gu, Y.; Huang, X.; Berry, V.; Liu, J.; Teffera, Y.; Huang, L.; Egge, B.; Mullady, E. L.; Schneider, S.; Andrews, P. S.; Mishra, A.; Newcomb, J.; Serafino, R.; Strathdee, C. A.; Turci, S. M.; Wilson, C.; DiMauro, E. F. J. Med. Chem. 2013, 56, 4320.
(d) Fisher, J. F.; Mobashery, S. Chem. Rev. 2021, 121, 3412.
(e) Tan, M.; Peters, B. B. C.; Andersson, P. G.; Zhou, T. Org. Chem. Front. 2024, 11, 2934.
(f) Shen, J.; Wang, Y.; Wu, Z.; Xu, D.; Zhang, W. Chin. J. Org. Chem. 2025, 45, 2637.
[2] (a) France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
(b) Pitts, C. R.; Lectka, T. Chem. Rev. 2014, 114, 7930.
(c) Martelli, G.; Orena, M.; Rinaldi, S. Curr. Org. Chem. 2014, 18, 1373.
(d) Ye, L.-W.; Shu, C.; Gagosz, F. Org. Biomol. Chem. 2014, 12, 1833.
(e) Saura-Sanmartin, A.; Andreu-Ardil, L. Org. Biomol. Chem. 2023, 21, 3296.
[3] (a) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
(b) Ager, D. J.; de Vries, A. H. M.; de Vries, J. G. Chem. Soc. Rev. 2012, 41, 3340.
(c) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016, 116, 14769.
(d) Yuan, Q.; Zhang, W. Chin. J. Org. Chem. 2016, 36, 274.
(e) Chu, Y.; Han, Z.; Ding, K. Chin. J. Org. Chem. 2023, 43, 1934.
(f) Behera, P.; Ramakrishna, D. S.; Chandrasekhar, M. M.; Kothakapu, S. R. Chirality 2023, 35, 477.
(g) Chakrabortty, S.; de Bruin, B.; de Vries, J. G. Angew. Chem. Int. Ed. 2024, 63, e202315773.
(h) Zhang, J.; Song, Y.; Zhang, Z.; Zhang, W. Asian J. Org. Chem. 2025, 14, e202400584.
(i) Chen, Q.; Yang, B.; Lang, Q.; Ding, X.; Li, X.; Zhang, X. Chin. J. Org. Chem. 2025, 45, 3326.
[4] Adam, D. Chemistry Nobel 2001. Nature 2001.
[5] (a) Johnson, N. B.; Lennon, I. C.; Moran, P. H.; Ramsden, J. A. Acc. Chem. Res. 2007, 40, 1291.
(b) Biosca, M.; Diéguez, M.; Zanotti-Gerosa, A. Adv. Catal. 2021, 68, 341.
(c) Zhang, M.; Yin, Q. Chin. J. Org. Chem. 2024, 44, 3258.
[6] Privileged Chiral Ligands and Catalysts; Ed.:Zhou, Q.-L., Wiley-VCH: Weinheim, Germany, 2011.
[7] (a) Lückemeier, L.; Pierau, M.; Glorius, F. Chem. Soc. Rev. 2023, 52, 4996.
(b) Wang, P.; He, Z.-L.; Xia, Z.-F.; Wei, J.; Dong, X.-Q. Chin. J. Chem. 2024, 42, 3135.
(c) Li, L.-J.; He, Y.; Yang, Y.; Guo, J.; Lu, Z.; Wang, C.; Zhu, S.; Zhu, S.-F. CCS Chem. 2024, 6, 537.
[8] Tian, F.; Yao, D.; Liu, Y.; Xie, F.; Zhang, W. Adv. Synth. Catal. 2010, 352, 1841.
[9] Li, Q.; Wan, P.; He, Y.; Zhou, Y.; Li, L.; Chen, B.; Duan, K.; Cao, R.; Zhou, Z.; Qiu, L. Asian J. Org. Chem. 2014, 3, 774.
[10] Liu, X.; Han, Z.; Wang, Z.; Ding, K. Angew. Chem. Int. Ed. 2014, 53, 1978.
[11] Bao, D.-H.; Gu, X.-S.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2017, 19, 118.
[12] Yuan, Q.; Liu, D.; Zhang, W. Org. Lett. 2017, 19, 1144.
[13] Yuan, Q.; Liu, D.; Zhang, W. Org. Lett. 2017, 19, 1886.
[14] Xia, J.; Nie, Y.; Yang, G.; Liu, Y.; Gridnev, I. D.; Zhang, W. Chin. J. Chem. 2018, 36, 612.
[15] Biosca, M.; Pàmies, O.; Diéguez, M. J. Org. Chem. 2019, 84, 8259.
[16] Faiges, J.; Borràs, C.; Pastor, I. M.; Pàmies, O.; Besora, M.; Diéguez, M. Organometallics 2021, 40, 3424.
[17] Biosca, M.; de la Cruz-Sánchez, P.; Faiges, J.; Margalef, J.; Salomó, E.; Riera, A.; Verdaguer, X.; Ferré, J.; Maseras, F.; Besora, M.; Pàmies, O.; Diéguez, M. ACS Catal. 2023, 13, 3020.
[18] Zhang, R.; Xu, S.; Luo, Z.; Liu, Y.; Zhang, J. Angew. Chem. Int. Ed. 2023, 62, e202213600.
[19] Zhang, K.; Cui, P.; Miao, M.; Zeng, M.; Wang, X.; Zhang, M.; Chen, Q.; Song, H.; Ke, B.; Qin, Y. Org. Chem. Front. 2024, 11, 1456.
[20] Massaro, L.; Mallick, R. K.; Yang, J.; Peters, B. B. C.; Ferrara, F.; Xiao, Y.; Andersson, P. G. ACS Catal. 2026, 16, 1264.
[21] Campello, H. R.; Parker, J.; Perry, M.; Ryberg, P.; Gallagher, T. Org. Lett. 2016, 18, 4124.
[22] Lang, Q.; Gu, G.; Cheng, Y.; Yin, Q.; Zhang, X. ACS Catal. 2018, 8, 4824.
[23] Huang, Y.; Li, P.; Dong, X.-Q.; Zhang, X. Org. Biomol. Chem. 2018, 16, 8819.
[24] Yang, J.; Li, X.; You, C.; Li, S.; Guan, Y.-Q.; Lv, H.; Zhang, X. Org. Biomol. Chem. 2020, 18, 856.
[25] Yin, C.; Pan, Y.; Zhang, X.; Yin, Q. Org. Lett. 2022, 24, 675.
[26] Xie, C.; Guo, Q.; Yang, Z.; Zi, G.; Huang, Y.; Hou, G. Org. Chem. Front. 2023, 10, 2498.
[27] Feng, K.; Chen, L.; Liu, T.; Zhang, X.; Feng, W.; Huang, A.; Shen, F.; Song, D.; Ling, F.; Zhong, W. Org. Lett. 2026, 28, 6574.
[28] Magnus, N. A.; Astleford, B. A.; Laird, D. L. T.; Maloney, T. D.; McFarland, A. D.; Rizzo, J. R.; Ruble, J. C.; Stephenson, G. A.; Wepsiec, J. P. J. Org. Chem. 2013, 78, 5768.
[29] Lynch, D.; Deasy, R. E.; Clarke, L.-A.; Slattery, C. N.; Khandavilli, U. B. R.; Lawrence, S. E.; Maguire, A. R.; Magnus, N. A.; Moynihan, H. A. Org. Lett. 2016, 18, 4978.
[30] Lou, Y.; Hu, Y.; Lu, J.; Guan, F.; Gong, G.; Yin, Q.; Zhang, X. Angew. Chem. Int. Ed. 2018, 57, 14193.
[31] Shi, Y.; Tan, X.; Gao, S.; Zhang, Y.; Wang, J.; Zhang, X.; Yin, Q. Org. Lett. 2020, 22, 2707.
[32] Chakrabortty, S.; Zheng, S.; Kallmeier, F.; Baráth, E.; Tin, S.; de Vries, J. G. ChemSusChem 2023, 16, e202202353.
[33] Ding, Z.; Luo, Y.; Yuan, Q.; Wang, G.; Yu, Z.; Zhao, M.; Liu, D.; Zhang, W. J. Am. Chem. Soc. 2024, 146, 25312.
[34] Wagener, T.; Lückemeier, L.; Daniliuc, C. G.; Glorius, F. Angew. Chem. Int. Ed. 2021, 60, 6425.
[35] Guo, S.; Ma, B.; Chen, G.-Q.; Zhang, X. Org. Lett. 2023, 25, 2426.
[36] Wang, F.; Tan, X.; Wu, T.; Zheng, L.-S.; Chen, G.-Q.; Zhang, X. Chem. Commun. 2020, 56, 15557.
Options
文章导航

/

〈 〉