Nickel-Catalyzed Reductive Cross-Coupling of Imines with α-Imino Esters for the Construction of α,β-Diamino Acid Derivatives

Abstract

A nickel-catalyzed reductive cross-coupling reaction of different imines has been developed. This method enables the first reductive cross-coupling between aryl/alkyl imines and α-imino esters, affording α,β-diamino acid derivatives bearing quaternary carbon centers in a single-step process. This imine umpolung strategy exhibits several advantages, such as mild conditions and broad functional group compatibility.

Keywords

Nickel catalysis - Imines - α-Imino esters - Reductive cross-coupling - α,β-Diamino acid derivatives

Publikationsverlauf

Eingereicht: 29. Mai 2025

Angenommen nach Revision: 04. Juli 2025

Artikel online veröffentlicht:
08. August 2025

• References

• 1a Viso A, de la Pradilla RF, García A, Flores A. Chem Rev 2005; 105: 3167
• 1b Wang J, Zhang L, Jiang H, Liu H. Curr Pharm Des 2010; 16: 1252
• 1c Viso A, de la Pradilla RF, Tortosa M, García A, Flores A. Chem Rev 2011; 111: 1
• 1d Izumi S, Kobayashi Y, Takemoto Y. Org Lett 2016; 18: 696
• 1e Wu G, Wang J, Liu C. et al. Org Chem Front 2019; 6: 2245
• 1f Eder I, Haider V, Zebrowski P, Waser M. Eur J Org Chem 2021; 2021: 202
• 1g Tian X, Xu X, Jing T, Kang Z, Hu W. Green Synth Catal 2021; 2: 337
• 1h Sha H, Xie X, Zhang D, Hu W, Kang Z. Adv Synth Catal 2023; 365: 4609
• 1i Hu H, Wu X, Wang B, Zhao L, Wang J, Jiang Z. Adv Synth Catal 2023; 365: 2622
• 1j Lichstrahl MS, Kahlert L, Li R, Zandi TA, Yang J, Townsend CA. Chem Sci 2023; 14: 3923
• 1k Hickey JL, Sindhikara D, Zultanski SL, Schultz DM. ACS Med Chem Lett 2023; 14: 557
• 2a Evans CS, Qureshi MY, Bell EA. Phytochemistry 1977; 16: 565
• 2b Martinez AP, Lee WW. J Org Chem 2002; 30: 317
• 2c Dawlaty J, Zhang X, Fischbach MA, Clardy J. J Nat Prod 2010; 73: 441
• 3a Jarvo ER, Copeland GT, Papaioannou N, Bonitatebus PJ, Miller SJ. J Am Chem Soc 1999; 121: 11638
• 3b Kretsinger JK, Schneider JP. J Am Chem Soc 2003; 125: 7907
• 3c Rosita D, Dewit MA, Luyt LG. J Med Chem 2009; 52: 2196
• 4a Strazzolini P, Malabarba A, Ferrari P, Grandi M, Cavalleri BJ. J Med Chem 1984; 27: 1295
• 4b Marastoni M, Bazzaro M, Bortolotti F, Salvadori S, Tematis R. Eur J Med Chem 1999; 34: 651
• 4c Visser F, Sun LJ, Damaraju V. et al. J Biol Chem 2007; 282: 14148

For selected examples, see:
• 5a Bernardi L, Gothelf AS, Hazell RG, Jørgensen KA. J Org Chem 2003; 68: 2583
• 5b Okada A, Shibuguchi T, Ohshima T, Masu H, Yamaguchi K, Shibasaki M. Angew Chem Int Ed 2005; 44: 4564
• 5c Salter MM, Kobayashi J, Shimizu Y, Kobayashi S. Org Lett 2006; 8: 3533
• 5d Cutting GA, Stainforth NE, John MP, Kociok-Köhn G, Willis MC. J Am Chem Soc 2007; 129: 10632
• 5e Hernández-Toribio J, Arrayás RG, Carretero JC. J Am Chem Soc 2008; 130: 16150
• 5f Kobayashi S, Yazaki R, Seki K, Yamashita Y. Angew Chem Int Ed 2008; 47: 5613
• 5g Yan XX, Peng Q, Li Q. et al. J Am Chem Soc 2008; 130: 14362
• 5h Jiang J, Xu H-D, Xi J-B. et al. J Am Chem Soc 2011; 133: 8428
• 5i Kato S, Yoshino T, Shibasaki M, Kanai M, Matsunaga S. Angew Chem Int Ed 2012; 51: 7007
• 5j Hayashi M, Iwanaga M, Shiomi N, Nakane D, Masuda H, Nakamura S. Angew Chem Int Ed 2014; 53: 8411
• 5k Tao Z, Adele A, Wu X, Gong L. Chin J Chem 2014; 32: 969
• 5l Kano T, Kobayashi R, Maruoka K. Angew Chem Int Ed 2015; 54: 8471
• 5m Nakamura S, Yamaji R, Iwanaga M. Chem Commun 2016; 52: 7462
• 5n Shao Q, Wu L, Chen J. et al. Adv Synth Catal 2018; 360: 4625
• 5o Chen JF, Gong X, Li JY. et al. Science 2018; 360: 1438
• 5p Fan Y, Lu J, Sha F, Li Q, Wu X-Y. J Org Chem 2019; 84: 11639
• 5q Zhang C, Yang J, Zhou W. et al. Org Lett 2019; 21: 8620
• 5r Li Z, Peng J, He C, Xu J, Ren H. J Org Chem 2020; 85: 3894
• 5s Zhu W-R, Liu K, Weng J. et al. Org Lett 2020; 22: 5014
• 5t Han X-L, Hu B, Fei C. et al. J Am Chem Soc 2023; 145: 4400
• 5u Foubelo F, Najera C, Retamosa MG, Sansano JM, Yus M. Chem Soc Rev 2024; 53: 7983
• 5v Liu S, Gao J, Zou Y, Hai Y. J Am Chem Soc 2024; 146: 20263

For selected examples, see:
• 6a Nishiwaki N, Knudsen KR, Gothelf KV, Jorgensen KA. Angew Chem Int Ed 2001; 40: 2992
• 6b Knudsen KR, Risgaard T, Nishiwaki N, Gothelf KV, Jorgensen KA. J Am Chem Soc 2001; 123: 5843
• 6c Chen Z, Morimoto H, Matsunaga S, Shibasaki M. J Am Chem Soc 2008; 130: 2170
• 6d Uraguchi D, Koshimoto K, Ooi T. J Am Chem Soc 2008; 130: 10878
• 6e Singh A, Johnston JN. J Am Chem Soc 2008; 130: 5866
• 6f Nunez MG, Farley AJM, Dixon DJ. J Am Chem Soc 2013; 135: 16348
• 6g Arai T, Matsumura E, Masu H. Org Lett 2014; 16: 2768
• 6h Lu N, Fang Y, Gao Y. et al. J Org Chem 2018; 83: 1486
• 7a Knappke CEI, Grupe S, Gaertner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem Eur J 2014; 20: 6828
• 7b Poremba KE, Dibrell SE, Reisman SE. ACS Catal 2020; 10: 8237
• 7c Ehehalt LE, Beleh OM, Priest IC. et al. Chem Rev 2024; 124: 13397
• 8a Hu H, Wang Z. J Am Chem Soc 2023; 145: 20775
• 8b Xiao J, Wang M, Yin X. et al. Angew Chem Int Ed 2023; 135: e202300743
• 8c Zhang L, Wang X, Pu M. et al. J Am Chem Soc 2023; 145: 8498
• 8d Wu X, Xia H, Gao C. et al. Nat Chem 2024; 16: 398
• 8e Zhang C, Wu X, Qu J, Chen Y. J Am Chem Soc 2024; 146: 25918
• 8f Xia T, Wu Y, Hu J, Wu X, Qu J, Chen Y. Angew Chem Int Ed 2024; 63: e202316012
• 8g Xia T, Wu W, Wu X, Qu J, Chen Y. Angew Chem Int Ed 2024; 63: e202318991
• 9a Chen D, Xu G, Zhou Q, Chung LW, Tang W. J Am Chem Soc 2017; 139: 9767
• 9b Zhou QH, Tang WJ, Chung LW. J Organomet Chem 2018; 864: 97
• 9c Zhu J, Huang L, Dong W. et al. Angew Chem Int Ed 2019; 58: 16119
• 9d Zhou M, Li K, Chen D, Xu R, Xu G, Tang W. J Am Chem Soc 2020; 142: 10337
• 9e Zhou M, Lin Y, Chen X-X, Xu G, Chung LW, Tang W. Angew Chem Int Ed 2023; 62: e202300334
• 10a Huang C, Tao Y, Cao X, Zhou C, Lu Q. J Am Chem Soc 2024; 146: 1984-1991
• 10b Tao Y, Ma W, Sun R, Huang C, Lu Q. Angew Chem Int Ed 2024; 63: e2409222
• 11a McManus HA, Guiry PJ. J Org Chem 2002; 67: 8566
• 11b Lu S-F, Du D-M, Zhang S-W, Xu J. Tetrahedron: Asymmetry 2004; 15: 3433
• 12 Duan A, Xiao F, Lan Y, Niu L. Chem Soc Rev 2022; 51: 9986