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

REVIEW

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

  • Liu Chunmeng ,
  • Wei Yuqing ,
  • Yuan Qianjia ,
  • Mao Guoliang ,
  • Zhang Wanbin
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  • 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.

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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

Cite this article

Liu Chunmeng , Wei Yuqing , Yuan Qianjia , Mao Guoliang , Zhang Wanbin . Research Progress on the Synthesis of Chiral Lactams via Transition Metal-Catalyzed Asymmetric Hydrogenation[J]. Chinese Journal of Organic Chemistry, 0 : 0 . DOI: 10.6023/cjoc202606009

References

[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.
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