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Synthesis
DOI: 10.1055/a-2646-6085
DOI: 10.1055/a-2646-6085
Short Review
Recent Progress and Applications of Asymmetric Hydrogenation and Transfer Hydrogenation through Dynamic Kinetic Resolution
Abstract
Given the growing demand for enantiomerically enriched compounds, the design of efficient, atom-economical, and sustainable synthetic strategies for the preparation of chiral alcohols and amines remains a critical objective in modern chemistry. This short, updated review highlights recent advances in homogeneous asymmetric catalysis employing transition-metal complexes in asymmetric hydrogenation (AH) and transfer hydrogenation (ATH) of ketones and imines under dynamic kinetic resolution (DKR) conditions to access these important building blocks. These methods enable the simultaneous formation of multiple stereogenic centers and have been significantly expanded through the development of novel catalytic systems and their application to previously unexplored classes of substrates.
Keywords
Asymmetric hydrogenation - Asymmetric transfer hydrogenation - Dynamic kinetic resolution - Chiral alcohols - Chiral amines - Stereoselectivity - Ketones - IminesPublication History
Received: 27 May 2025
Accepted after revision: 01 July 2025
Article published online:
12 August 2025
© 2025. Thieme. All rights reserved.
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References
- 1a de Vries JG, Elsevier CJ. The Handbook of Homogeneous Hydrogenation. Vol. 1. Weinheim: Wiley-VCH; 2007
- 1b Modern Reduction Methods; Andersson PG, Munslow IJ. eds Weinheim: Wiley-VCH; 2008
- 1c For comprehensive reviews and chapters on asymmetric hydrogenation (AH), see: Knowles WS. Angew Chem Int Ed 2002; 41: 1998
- 1d Noyori R. Angew Chem Int Ed 2008; 2002: 41
- 1e Genêt J-P. Acc Chem Res 2003; 36: 908
- 1f Blaser H-U, Malan C, Pugin B, Spindler F, Steiner H, Studer M. Adv Synth Catal 2003; 345: 103
- 1g Zhou Y-G. Acc Chem Res 2007; 40: 1357
- 1h Shang G, Li W, Zhang X. Catalytic Asymmetric Synthesis. Ojima I. ed 3rd ed New York: John Wiley & Sons; 2010: 343
- 1i Xie JH, Zhu SF, Zhou QL. Chem Rev 2011; 111: 1713
- 1j Gopalaiah K, Kagan HB. Chem Rev 2011; 111: 4599
- 1k Wang D-S, Chen Q-A, Lu S-M, Zhou Y-G. Chem Rev 2012; 112: 2557
- 1l Chen Q-A, Ye Z-S, Duan Y, Zhou Y-G. Chem Soc Rev 2013; 42: 497
- 1m Hamada Y. Chem Rec 2014; 14: 235
- 1n Li Y-Y, Yu S-L, Shen W-Y, Gao J-X. Acc Chem Res 2015; 48: 2587
- 1o Xie J-H, Bao D-H, Zhou Q-L. Synthesis 2015; 47: 460
- 1p Zhang Z, Butt NA, Zhang W. Chem Rev 2016; 116: 14769
- 1q Li W, Lu B, Zhang Z. Chem Rec 2016; 16: 2506
- 1r Mashima K, Higashida K, Iimuro A, Nagae H, Kita Y. Chem Rec 2016; 16: 2585
- 1s Luo Y-E, He Y-M, Fan Q-H. Chem Rec 2016; 16: 2697
- 1t Ohkuma T, Arai N. Chem Rec 2016; 16: 2801
- 1u Imamoto T. Chem Rec 2016; 16: 2659
- 1v Xie X, Lu B, Li W, Zhang Z. Coord Chem Rev 2018; 355: 39
- 1w Seo CSG, Morris RH. Organometallics 2019; 38: 47
- 1x Wen J, Wang F, Zhang X. Chem Soc Rev 2021; 50: 3211
- 1y Behera P, Ramakrishna DS, Chandrasekhar MM, Kothakapu SR. Chirality 2023; 35: 477
- 1z Chen J, Wei H, Gridnev ID, Zhang W. Angew Chem Int Ed 2025; e202425589
- 2a For comprehensive reviews and chapters on asymmetric transfer hydrogenation (ATH), see: Zassinovich G, Mestroni G, Gladiali S. Chem Rev 1992; 92: 1051
- 2b de Graauw CF, Peters JA, van Bekkum H, Huskens J. Synthesis 1994; 1007
- 2c Noyori R, Hashiguchi S. Acc Chem Res 1997; 30: 97
- 2d Palmer MJ, Wills M. Tetrahedron Asymmetry 1999; 10: 2045
- 2e Pàmies O, Bäckvall J-E. Chem Eur J 2001; 7: 5052
- 2f Everaere K, Mortreux A, Carpentier J-F. Adv Synth Catal 2003; 345: 67
- 2g Gladiali S, Alberico E. Chem Soc Rev 2006; 35: 226
- 2h Samec JSM, Bäckvall J-E, Andersson PG, Brandt P. Chem Soc Rev 2006; 35: 237
- 2i Ikariya T, Blacker AJ. Acc Chem Res 2007; 40: 1300
- 2j Blacker AJ. The Handbook of Homogeneous Hydrogenation. de Vries JG, Elsevier CJ. eds Weinheim: Wiley-VCH; 2007: 1215
- 2k Wang C, Wu X, Xiao J. Chem Asian J 2008; 3: 1750
- 2l Ikariya T. Bull Chem Soc Jpn 2011; 84: 1
- 2m Zheng C, You S-L. Chem Soc Rev 2012; 41: 2498
- 2n Bartoszewicz A, Ahlsten N, Martín-Matute B. Chem Eur J 2013; 19: 7274
- 2o Slagbrand T, Lundberg H, Adolfsson H. Chem Eur J 2014; 20: 16102
- 2p Štefane B, Požgan F. Catal Rev 2014; 56: 82
- 2q Ito J-I, Nishiyama H. Tetrahedron Lett 2014; 55: 3133
- 2r Cotarca L, Verzini M, Volpicelli R. Chim Oggi 2014; 32: 36
- 2s Wang D, Astruc D. Chem Rev 2015; 115: 6621
- 2t Foubelo F, Nájera C, Yus M. Tetrahedron Asymmetry 2015; 26: 769
- 2u Nedden HG, Zanotti-Gerosa A, Wills M. Chem Rec 2016; 16: 2623
- 2v Štefane B, Požgan F. Top Curr Chem 2016; 18: 374
- 2w Ayad T, Phansavath P, Ratovelomanana-Vidal V. Chem Rec 2016; 16: 2754
- 2x Matuška O, Kindl M, Kačer P. New Advances in Hydrogenation Process. Ravanchi TM. ed Croatia: InTech; 2017: 37
- 2y Milner L, Talavera G, Nedden HG. Chim Oggi 2017; 35: 37
- 2z Matsunami A, Kayaki Y. Tetrahedron Lett 2018; 59: 504
- 2aa Whittlesey MK. Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1. Nolan SP, Cazin CSJ. eds Stuttgart: Georg Thieme Verlag; 2018: 285
- 2ab Zhang Z, Butt NA, Zhou M, Liu D, Zhang W. Chin J Chem 2018; 36: 443
- 2ac Talavera G, Santana Fariña A, Zanotti-Gerosa A, Nedden HG. Top Organomet Chem 2019; 65: 73
- 2ad Caleffi GS, Demidoff FC, Nájera C, Costa PRR. Org Chem Front 2022; 9: 1165
- 2ae Yang S, Fang X. Tetrahedron 2023; 145: 133609
- 2af Bacheley L, Guillamot G, Phansavath P, Ratovelomanana-Vidal V. Tetrahedron 2024; 152: 133781
- 3a For previous comprehensive reviews covering this topic, see: Noyori R, Tokunaga M, Kitamura M. Bull Chem Soc Jpn 1995; 68: 36
- 3b Caddick S, Jenkins K. Chem Soc Rev 1996; 25: 447
- 3c Ward RS. Tetrahedron Asymmetry 1995; 6: 1475
- 3d Sturmer R. Angew Chem Int Ed Engl 1997; 36: 1173
- 3e El Gihani MT, Williams JMJ. Curr Opin Chem Biol 1999; 3: 11
- 3f Ratovelomanana-Vidal V, Genêt J-P. Can J Chem 2000; 78: 846
- 3g Huerta FF, Minidis ABE, Bäckvall J-E. Chem Soc Rev 2001; 30: 321
- 3h Faber K. Chem Eur J 2001; 7: 5005
- 3i Pàmies O, Bäckvall J-E. Chem Rev 2003; 103: 3247
- 3j Pellissier H. Tetrahedron 2003; 59: 8291
- 3k Turner NJ. Curr Opin Chem Biol 2004; 8: 114
- 3l Vedejs E, Jure M. Angew Chem Int Ed 2005; 44: 3974
- 3m Martín-Matute B, Bäckvall J-E. Curr Opin Chem Biol 2007; 11: 226
- 3n Pellissier H. Tetrahedron 2008; 64: 1563
- 3o Pellissier H. Tetrahedron 2011; 67: 3769
- 3p Xie J-H, Zhou Q-L. Aldrichim Acta 2015; 48: 33
- 3q Echeverria P-G, Ayad T, Phansavath P, Ratovelomanana-Vidal V. Synthesis 2016; 48: 2523
- 3r Bhat V, Welin ER, Guo X, Stoltz BM. Chem Rev 2017; 117: 4528
- 3s Molina Betancourt R, Echeverria PG, Ayad T, Phansavath P, Ratovelomanana-Vidal V. Synthesis 2021; 53: 30
- 4 Noyori R, Ikeda T, Ohkuma T. et al. J Am Chem Soc 1989; 111: 9134
- 5 Jugé S, Gênet J-P, Mallard S. EP 0489071A1, 1992; the original French patent application FP 19890011159 was filed in 1989
- 6 Swamy CAP, Varenikov A, de Ruiter G. Chem Eur J 2020; 26: 2333
- 7 Li X, Zhao Z-B, Chen M-W. et al. Chem Commun 2020; 56: 5815
- 8 Wang J, Shao P-L, Lin X, Ma B, Wen J, Zhang X. Angew Chem Int Ed 2020; 59: 18166
- 9 Tan X, Zeng W, Wen J, Zhang X. Org Lett 2020; 22: 7230
- 10 Xiong Y, Lin H, Zhu C-L. et al. Org Lett 2021; 23: 8883
- 11 Yang D, Yang A-J, Chen Y, Xie J-H, Zhou Q-L. Org Lett 2021; 23: 1616
- 12 Xu Y, Luo Y, Ye J, Deng Y, Liu D, Zhang W. J Am Chem Soc 2022; 144: 20078
- 13 Li J, Ye J, Zhou J, Li J, Liu D, Zhang W. Chem Commun 2022; 58: 4905
- 14 Wang K, Niu S, Guo X. et al. J Org Chem 2022; 87: 3804
- 15 He B, Chen G-Q, Zhang X. Chem Commun 2024; 60: 9785
- 16 Ishikawa H, Yurino T, Komatsu R. et al. Org Lett 2023; 25: 2355
- 17 Wang H, Xun S-S, Yu C-B, Zhou Y-G. Chem Sci 2024; 15: 11038
- 18 Zhang L, Wang Z, Han Z, Ding K. Angew Chem Int Ed 2020; 59: 15565
- 19 Yang P, Song D, Chen L. et al. Org Chem Front 2024; 11: 2201
- 20 He B, Song J, Yin C, Chen G-Q, Zhang X. Org Chem Front 2022; 9: 6247
- 21 Wang F, Tan X, Wu T, Zheng L-S, Chen G-Q, Zhang X. Chem Commun 2020; 56: 15557
- 22 Yang D, Wu X, Zheng X-J, Xie J-H, Zhou Q-L. Org Lett 2021; 23: 5153
- 23 Bin H-Y, Cheng L, Wu X. et al. Chem Sci 2021; 12: 7793
- 24 Yurino T, Nishihara R, Yasuda T. et al. Org Lett 2024; 26: 2872
- 25 Wang J, Shi Y, Wang F. et al. Angew Chem Int Ed 2023; 62: e202303868
- 26 Hu L, Wang YZ, Xu L, Yin Q, Zhang X. Angew Chem Int Ed 2022; 61: e202202552
- 27 Rong N, Zhou A, Liang M, Wang S-G, Yin Q. J Am Chem Soc 2024; 146: 5081
- 28 Doering WE, Young RW. J Am Chem Soc 1950; 72: 631
- 29 Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R. J Am Chem Soc 1995; 117: 7562
- 30 Schwink L, Ireland T, Püntener K, Knochel P. Tetrahedron: Asymmetry 1998; 9: 1143
- 31 Murata K, Okano K, Miyagi M, Iwane H, Noyori R, Ikariya T. Org Lett 1999; 1: 1119
- 32 Gediya SK, Clarkson GJ, Wills M. J Org Chem 2020; 85: 11309
- 33 Caleffi GS, Brum JDOC, Costa AT, Domingos JLO, Costa PRR. J Org Chem 2021; 86: 4849
- 34 Wang F, Yang T, Wu T. et al. J Am Chem Soc 2021; 143: 2477
- 35a Echeverria P-G, Férard C, Phansavath P, Ratovelomanana-Vidal V. Catal Commun 2015; 62: 95
- 35b Zheng L-S, Llopis Q, Echeverria P-G. et al. J Org Chem 2017; 82: 5607
- 35c Echeverria P-G, Zheng L-S, Llopis Q. et al. SynOpen 2022; 6: 75
- 36 Molina Betancourt R, Phansavath P, Ratovelomanana-Vidal V. Org Lett 2021; 23: 1621
- 37 Touge T, Nara H, Kida M, Matsumura K, Kayaki Y. Org Lett 2021; 23: 3070
- 38 Betancourt RM, Phansavath P, Ratovelomanana-Vidal V. J Org Chem 2021; 86: 12054
- 39 Molina Betancourt R, Phansavath P, Ratovelomanana-Vidal V. Molecules 2022; 27: 995
- 40 Molina Betancourt R, Bacheley L, Karapetyan A, Guillamot G, Phansavath P, Ratovelomanana-Vidal V. ChemCatChem 2022; 14: e202200595
- 41 Wang F, Zhang Z, Chen Y. et al. Nat Commun 2022; 13: 7794
- 42 Chen T, Liu W, Gu W. et al. J Am Chem Soc 2023; 145: 585
- 43 Bacheley L, Molina Betancourt R, Ravindra R, Guillamot G, Phansavath P, Ratovelomanana-Vidal V. Eur J Org Chem 2023; 26: e202300383
- 44 Kim SW, Foker EA, Wolf WJ. et al. Org Lett 2024; 26: 3103
- 45 Pan HJ, Lin Y, Gao T. et al. Angew Chem Int Ed 2021; 60: 18599
- 46 Gao Y, Hong G, Zhang L. et al. CCS Chem 2025; 7: 80
- 47 Luo Z, Sun G, Wu S. et al. Adv Synth Catal 2021; 363: 3030
- 48 More GV, Malekar PV, Kalshetti RG, Shinde MH, Ramana CV. Tetrahedron Lett 2021; 66: 152831
- 49 Hu Z-Q, Li X, Liu L-X, Yu C-B, Zhou Y-G. J Org Chem 2021; 86: 17453
- 50 Xie Q-X, Liu L-X, Zhu Z-H, Yu C-B, Zhou Y-G. J Org Chem 2022; 87: 7521
- 51 Lapa DP, Araújo LHS, Melo SR, Costa PRR, Caleffi GS. Molecules 2024; 29: 3420
- 52 Malekar PV, More GV, Ramana CV. Tetrahedron 2024; 167: 134293
- 53 Hu R, Wang F, Pan F. et al. Org Lett 2024; 26: 7457
- 54 Li J, Zhao C. ACS Catal 2023; 13: 14155
- 55 Rodríguez-Franco C, Roldán-Molina E, Aguirre-Medina A, Fernández R, Hornillos V, Lassaletta JM. Angew Chem Int Ed 2024; 63: e202409524
- 56 Li X, Yang J, He Z. et al. Adv Synth Catal 2025; 367: e202401307
- 57 Lerchen A, Gandhamsetty N, Farrar EHE. et al. Angew Chem Int Ed 2020; 59: 23107
- 58 Jiang H-X, Han D-D, Song R-P. et al. Adv Synth Catal 2023; 365: 1398
- 59 Liang M-R, Du X, Lin J. et al. J Am Chem Soc 2025; 147: 4239