REVIEWS

Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update

  • Shuang Yang ,
  • Xinqiang Fang
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  • State Key Laboratory of Structural Chemistry, and Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100
* Corresponding authors. ;

Received date: 2023-08-25

  Revised date: 2023-09-30

  Online published: 2023-10-26

Supported by

National Natural Science Foundation of China(22071242); National Natural Science Foundation of China(21871260); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000); Fujian Provincial Natural Science Foundation(2021J01522)

Abstract

Kinetic resolution is one of the most commonly used methods allowing access to enantioenriched compounds. The last two decades have seen the rapid development of kinetic resolutions enabled by N-heterocyclic carbene catalysis, and part of the achievements have been summarized in our previous review paper published in 2017. Since then, a series of new advances have been realized, and this review will provide an update of this field covering reports from mid-2017 to 2023.

Cite this article

Shuang Yang , Xinqiang Fang . Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 448 -480 . DOI: 10.6023/cjoc202308023

References

[1]
(a) Kagan, H. B.; Fiaud, J. C.In Kinetic Resolution, Topics in Stereochemistry, Eds.: Eliel, E. L.; Wilen, S. H., Wiley, New York, 1988, pp. 249-330.
[1]
(b) Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers. Racemates, and Resolutions, Wiley, New York, 1981.
[2]
(a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
[2]
(b) Kagan H. B. Tetrahedro. 2001, 57, 2449.
[2]
(c) Faber K. Chem.-Eur. J. 2001, 7, 5004.
[2]
(d) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5.
[2]
(e) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407.
[2]
(f) Vedejs, E.; Jure, M. Angew. Chem.. Int. Ed. 2005, 44, 3974.
[2]
(g) Pellissier H. Adv. Synth. Catal. 2011, 353, 1613.
[2]
(h) Krasnov, V. P.; Gruzdev, D. A.; Levit, G. L. Eur. J. Org. Chem. 2012, 1471.
[2]
(i) Pellissier H. In Separation of Enantiomers: Synthetic Methods, 1st ed, Ed.: Todd, M., Wiley-VCH, Weinheim, 2014, pp. 75-122.
[2]
(j) Ma, G.; Sibi, M. P. Chem.-Eur. J. 2015, 21, 11644.
[2]
(k) Petersen K. S. Asian J. Org. Chem. 2016, 5, 308.
[2]
(l) Gurubrahamam, R.; Cheng, Y.-S.; Huang, W.-Y.; Chen, K. ChemCatChe. 2016, 8, 86.
[2]
(m) Kreituss, I.; Bode, J. W. Acc. Chem. Res. 2016, 49, 2807.
[2]
(n) Yang, H.; Zheng, W.-H. Tetrahedron Lett. 2018, 59, 583.
[2]
(o) Pellissier H. Tetrahedro. 2018, 74, 3459.
[2]
(o) Harwood, L. A.; Wong, L. L.; Robertson, J. Angew. Chem.. Int. Ed. 2021, 60, 4434.
[2]
(q) Chen, Y.; Liu, W.; Yang, X. Chin. J. Org. Chem. 2022, 42, 679 (in Chinese).
[2]
(陈运荣, 刘炜, 杨晓瑜, 有机化学. 2022, 42, 679.)
[2]
(p) Ding, B.; Xue, Q.; Jia, S.; Cheng, H.-G.; Zhou, Q. Synthesi. 2022, 54, 1721.
[2]
(s) Peng, T.; Li, S.; Yang, D.; Wang, L. Org. Chem. Front. 2023, 10, 3401.
[2]
(t) Li, H.; Yin, L. Chin. J. Org. Chem. 2022, 42, 3183 (in Chinese).
[2]
(李晖, 殷亮, 有机化学. 2022, 42, 3183.)
[2]
(u) Liu, H.; Shen, C.; Chang, X.; Wang, C. Chin. J. Org. Chem. 2022, 42, 3322. (in Chinese).
[2]
(刘华超, 沈冲, 常鑫, 王春江, 有机化学. 2022, 42, 3322.)
[2]
(v) Liu, W.; Wang, D.; Zhang, D.; Yang, X. Synlet. 2022, 33, 1788.
[3]
(a) Ward R. S. Tetrahedron: Asymmetr. 1995, 6, 1475.
[3]
(b) Pellissier H. Tetrahedro. 2003, 59, 8291.
[3]
(c) Pellissier H. Tetrahedro. 2008, 64, 1563.
[3]
(d) Pellissier H. Chirality from Dynamic Kinetic Resolution. Royal Society of Chemistry, Cambridge, 2011.
[3]
(e) Pellissier H. Tetrahedro. 2011, 67, 3769.
[3]
(f) Pellissier H. Adv. Synth. Catal. 2011, 353, 659.
[3]
(g) Nakano, K.; Kitamura, M. In Separation of Enantiomers: Synthetic Methods, 1st ed, Ed.: Todd, M., Wiley-VCH, Weinheim, 2014, p. 161.
[3]
(h) Pellissier H. Tetrahedro. 2016, 72, 3133.
[3]
(i) Li, P.; Hu, X.; Dong, X.-Q.; Zhang, X. Molecule. 2016, 21, 1327.
[3]
(j) Liu, W.; Yang, X. Asian J. Org. Chem. 2021, 10, 692.
[3]
(k) Pellissier H. Eur. J. Org. Chem. 2022, e202101561.
[4]
Millera, L. C.; Sarpong, R. Chem. Soc. Rev. 2011, 40, 4550.
[5]
(a) Zeitler K. Angew. Chem.. Int. Ed. 2005, 44, 7506.
[5]
(b) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
[5]
(c) Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336.
[5]
(d) Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem.. Int. Ed. 2012, 51, 11686.
[5]
(e) Douglas, J.; Churchill, G.; Smith, A. D. Synthesi. 2012, 44, 2295.
[5]
(f) Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53.
[5]
(g) Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906.
[5]
(h) De Sarkar, S.; Biswas, A.; Samanta, R. C.; Studer, A. Chem.- Eur. J. 2013, 19, 4664.
[5]
(i) Mahatthananchai, J.; Bode, J. W. Acc. Chem. Res. 2014, 47, 696.
[5]
(j) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Natur. 2014, 510, 485.
[5]
(k) Chauhan, P.; Enders, D. Angew. Chem.. Int. Ed. 2014, 53, 1485.
[5]
(l) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307.
[5]
(m) Wang, M. H.; Scheidt, K. A. Angew. Chem.. Int. Ed. 2016, 55, 14912
[5]
(n) Chen, X.-Y.; Liu, Q.; Chauhan, P.; Enders, D. Angew. Chem.. Int. Ed. 2018, 57, 3862.
[5]
(o) Wang, J.; Zhao, C.; Wang, J. ACS Catal. 2021, 11, 12520.
[5]
(p) Song, R.; Xie, Y.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2021, 60, 2.
[5]
(q) Li, Q.-Z.; Zeng, R.; Han, B.; Li, J.-L. Chem.-Eur. J. 2021, 27, 3238.
[5]
(r) Song, R.; Jin, Z.; Chi, Y. R. Chem. Sci. 2021, 12, 5037.
[5]
(s) Marzo L. Eur. J. Org. Chem. 2021, 4603.
[5]
(t) Zhang, B.; Yang, G.; Guo, D.; Wang, J. Org. Chem. Front. 2022, 9, 5016.
[5]
(u) Sharma, D.; Chatterjee, R.; Dhayalan, V.; Dandela, R. Synthesi. 2022, 54, 4129.
[5]
(v) Liu, Y.; Wang, Y.; Wu, X.; Chi, Y. R. Chem. Rec. 2023, 23, e202200219.
[5]
(w) Yang, X.; Zhang, Y.; Li, T.; Jin, Z. Adv. Synth. Catal. 2023, 365, 1756.
[5]
(x) Nie, G.; Li, T. Asian J. Org. Chem. 2023, 12, e202200680.
[5]
(y) Li, Q.-Z.; Kou, X.-X.; Qi, T.; Li, J.-L. ChemCatChe. 2023, 15, e202201320.
[5]
(z) De Risi, C.; Brandolese, A.; Di Carmine, G.; Ragno, D.; Massi, A.; Bortolini, O. Chem.-Eur. J. 2023, 29, e202202467.
[6]
(a) Yang, S.; Fang, X. Curr. Org. Synth. 2017, 14, 654.
[6]
(b) Wang, Z.; Pan, D.; Li, T.; Jin, Z. Chem. Asian J. 2018, 13, 2149.
[6]
(c) Chen, S.; Shi, Y.-H.; Wang, M. Chem. Asian J. 2018, 13, 2184.
[6]
(d) Risi, C. D.; Bortolini, O.; Di Carmine, G.; Ragno, D.; Massi, A. Synthesi. 2019, 51, 1871.
[7]
Dong, S.; Frings, M.; Zhang, D.; Guo, Q.; Daniliuc, C. G.; Cheng, H.; Bolm, C. Chem.-Eur. J. 2017, 23, 13888.
[8]
Liu, B.; Yan, J.; Huang, R.; Wang, W.; Jin, Z.; Zanoni, G.; Zheng, P.; Yang, S.; Chi, Y. R. Org. Lett. 2018, 20, 3447.
[9]
Bie, J.; Lang, M.; Wang, J. Org. Lett. 2018, 20, 5866.
[10]
Zhao, C.; Wang, J. Adv. Synth. Catal. 2019, 361, 1668.
[11]
Lu, S.; Poh, S. B.; Rong, Z.-Q.; Zhao, Y. Org. Lett. 2019, 21, 6169.
[12]
Yang, G.; Guo, D.; Meng, D.; Wang, J. Nat. Commun. 2019, 10, 3062.
[13]
Yuan, H.; Du, Y.; Liu, F.; Guo, L.; Sun, Q.; Feng, L.; Gao, H. Chem. Commun. 2020, 56, 8226.
[14]
Liu, Y.; Majhi, P. K.; Song, R.; Mou, C.; Hao, L.; Chai, H.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2020, 59, 3859.
[15]
Gao, Y.-Y.; Zhang, C.-L.; Dai, L.; Han, Y.-F.; Ye, S. Org. Lett. 2021, 23, 1361.
[16]
(a) Chen, X.; Fong, J. Z. M.; Xu, J.; Mou, C.; Lu, Y.; Yang, S.; Song, B.-A.; Chi, Y. R. J. Am. Chem. Soc. 2016, 138, 7212.
[16]
(b) Liu, B.; Song, R.; Xu, J.; Majhi, P. K.; Yang, X.; Yang, S.; Jin, Z.; Chi, Y. R. Org. Lett. 2020, 22, 3335.
[17]
Brandolese, A.; Ragno, D.; Leonardi, C.; Di Carmine, G.; Bortolini, O.; De Risi, C.; Massi, A. Eur. J. Org. Chem. 2020, 16, 2439.
[18]
Porey, A.; Mondal, B. D.; Guin, J. Angew. Chem.. Int. Ed. 2021, 60, 8786-8791.
[19]
Yang, X.; Majhi, P. K.; Chai, H.; Liu, B.; Sun, J.; Liu, T.; Liu, Y.; Zhou, L.; Xu, J.; Liu, J.; Wang, D.; Zhao, Y.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2021, 60, 159.
[20]
Guo, D.; Peng, Q.; Zhang, B.; Wang, J. Org. Lett. 2021, 23, 7765.
[21]
Liu, J.; Zhou, M.; Deng, R.; Zheng, P.; Chi, Y. R. Nat. Commun. 2022, 13, 4793.
[22]
Wang, Y.; Yamauchi, A.; Hashimoto, K.; Fujiwara, T.; Inokuma, T.; Mitani, Y.; Ute, K.; Kuwano, S.; Yamaoka, Y.; Takasu, K.; Yamada, K.-I. ACS Catal. 2022, 12, 6100.
[23]
Yamada, K.-I.; Yamauchi, A.; Fujiwara, T.; Hashimoto, K.; Wang, Y.; Kuwano, S.; Inokuma, T. Asian J. Org. Chem. 2022, 11, e202200452.
[24]
Zhu, P.; Li, W.; Lan, J.; Zhu, T. Nat. Commun. 2023, 13, 3827.
[25]
Zhang, G.; Xu, W.; Liu, J.; Das, D. K.; Yang, S.; Perveen, S.; Zhang, H.; Li, X.; Fang, X. Chem. Commun. 2017, 53, 13336.
[26]
Chen, X.-Y.; Li, S.; Liu, Q.; Kumar, M.; Peuronen, A.; Rissanen, K.; Enders, D. Chem.-Eur. J. 2018, 24, 9735.
[27]
Chen, K.-Q.; Gao, Z.-H.; Ye, S. Angew. Chem.. Int. Ed. 2019, 58, 1183.
[28]
(a) Cano, R.; Zakarian, A.; McGlacken, G. P. Angew. Chem.. Int. Ed. 2017, 56, 9278.
[28]
(b) Janey J. M. Angew. Chem.. Int. Ed. 2005, 44, 4292.
[28]
(c) Smith, A. M. R.; Hii, K. K. M. Chem. Rev. 2011, 111, 1637.
[29]
Liu, J.; Vasamsetty, L.; Anwar, M.; Yang, S.; Xu, W.; Liu, J.; Nagaraju, S.; Fang, X. ACS Catal. 2020, 10, 2882.
[30]
Vasamsetty, L.; Kong, X.; Meng, M.; Yang, S.; Xu, W.; Reddy, P. S.; Fang, X. Chem. Asian J. 2018, 13, 3838.
[31]
Zhao, Z.; Yang, S.; Lan, S.; Liu, J.; Liu, S.; Fang, X. Adv. Synth. Catal. 2019, 361, 3943.
[32]
Zehra, S. T.; Zhang, G.; Yang, S.; Fang X. Org. Biomol. Chem. 2019, 17, 2169.
[33]
Xu, W.; Li, Y.; Liu, R.; Yang, S.; Liu, J.; Fang, X. Org. Chem. Front. 2019, 6, 290.
[34]
Perveen, S.; Yang, S.; Meng, M.; Xu, W.; Zhang, G.; Fang, X. Commun. Chem. 2019, 2, 8.
[35]
Lv, Y.; Luo, G.; Liu, Q.; Jin, Z.; Zhang, X.; Chi, Y. R. Nat. Commun. 2022. 13, 36.
[36]
Mondal, S.; Mukherjee, S.; Das, T. K.; Gonnade, R.; Biju, A. T. ACS Catal. 2017, 7, 3995.
[37]
Lv, J.; Xu, J.; Pan, X.; Jin, Z.; Chi, Y. R. Sci. China Chem. 2021, 64, 985.
[38]
Wang, M. H.; Barsoum, D.; Schwamb, C. B.; Cohen, D. T.; Goess, B. C.; Riedrich, M.; Chan, A.; Maki, B. E.; Mishra, R. K.; Scheidt, K. A. J. Org. Chem. 2017, 82, 4689.
[39]
Bhattacharya, A.; mani Shukla, P.; Kaushika, L. K.; Maji, B. Org. Chem. Front. 2019, 6, 3523.
[40]
Zhang, Z.-J.; Wen, Y.-H.; Song, J.; Gong, L.-Z. Angew. Chem.. Int. Ed. 2021, 60, 3268.
[41]
(a) Fischer, C.; Smith, S. W.; Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 1472.
[41]
(b) Chen, X.-Y.; Ye, S. Org. Biomol. Chem. 2013, 11, 7991.
[42]
Scott, L.; Nakano, Y.; Zhang, C.; Lupton, D. W. Angew. Chem.. Int. Ed. 2018, 57, 10299.
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