Research Progress on Copper(I)-Catalyzed Asymmetric Allylation of Ketones or Ketimines

doi:10.6023/A24100300

Abstract

Chiral tertiary homoallylic alcohol and chiral α,α-disubstituted homoallylic amine scaffolds are ubiquitous in numerous bioactive natural products and pharmaceutically relevant molecules. Thus, asymmetric synthesis of these compounds has attracted an increasing attention from synthetic chemists. Compared to traditional methods, transition-metal-catalyzed asymmetric allylation of ketones or ketimines serves as a powerful methodology for constructing these compounds due to its excellent atom- and step-economy. Recent progress on copper(I)-catalyzed asymmetric allylation of ketones or ketimines is summarized. Based on the strategies for the generation of allyl-copper(I) species in situ, this review is divided into three sections: reactions through transmetalation, three-component coupling reactions, and proton-transfer reactions. The mechanisms and potential applications of some representative strategies are also included. Finally, the future developments in this field are outlooked.

Key words: copper(I) catalysis, ketones, ketimines, asymmetric allylation, transmetalation, three-component coupling, proton-transfer reaction

Cite this article

Hui Li, Liang Yin. Research Progress on Copper(I)-Catalyzed Asymmetric Allylation of Ketones or Ketimines[J]. Acta Chimica Sinica, 2024, 82(12): 1274-1288.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 24

Scheme 1. Strategies in copper(I)-catalyzed asymmetric allylation of ketones or ketimines

Scheme 2. Copper(I)-catalyzed asymmetric addition of allylsilanes or allylboronates to ketones

Scheme 3. Copper(I)-catalyzed asymmetric addition of 3,3-disubstituted allyldiboronates to ketones

Scheme 4. Copper(I)-catalyzed dynamic kinetic asymmetric allylation of ketones with allylboronates

Scheme 5. Copper(I)-catalyzed asymmetric addition of allylboronate to ketimines

Scheme 6. Copper(I)-catalyzed asymmetric three-component coupling reaction of ketones, allenes, and hydrosilanes

Scheme 7. Copper(I)-catalyzed asymmetric reductive coupling reaction of ketones and allenylsilanes

Scheme 8. Copper(I)-catalyzed asymmetric reductive coupling reaction of ketones and a cyclic allenamide

Scheme 9. Copper(I)-catalyzed asymmetric reductive coupling reaction of ketones and an acyclic allenamide

Scheme 10. Copper(I)-catalyzed asymmetric reductive coupling reaction of ketones and siloxypropadienes

Scheme 11. Copper(I)-catalyzed asymmetric reductive coupling reaction of ketones with conjugated dienes

Scheme 12. Copper(I)-catalyzed asymmetric intramolecular reductive coupling reaction of conjugated diene-tethered ketones

Scheme 13. Copper(I)-catalyzed asymmetric reductive coupling reaction of ketones and azatrienes

Scheme 14. Copper(I)-catalyzed asymmetric intramolecular reductive coupling reaction of conjugated diene-tethered ketimines

Scheme 15. CuH-catalyzed asymmetric reductive coupling reaction of ketimines with conjugated dienes

Scheme 16. Copper(I)-catalyzed asymmetric coupling reaction of ketones, allenes, and B2(pin)2

Scheme 17. Copper(I)-catalyzed asymmetric borylative cyclization of allene cyclohexanediones

Scheme 18. Copper(I)-catalyzed asymmetric carboboronation of allenes with ketimines and B2(pin)2

Scheme 19. Copper(I)-catalyzed asymmetric carboboronation of allenes with ketiminoesters and B2(pin)2

Scheme 20. Copper(I)-catalyzed asymmetric borylative coupling reaction of 1,3-dienes with ketones

Scheme 21. Copper(I)-catalyzed asymmetric borylative cyclization of conjugated dienes-tethered ketones

Scheme 22. Copper(I)-catalyzed asymmetric allylation reaction of ketones with 1,4-enynes

Scheme 23. Copper(I)-catalyzed stereoselective allylation reaction of ketones with 1,4-dienes

Scheme 24. Copper(I)-catalyzed asymmetric allylation reaction of ketones with 2-aza-1,4-dienes

References 47

[1]	(a) Mizui, Y.; Sakai, T.; Iwata, M.; Uenaka, T.; Okamoto, K.; Shimizu, H.; Yamori, T.; Yoshimatsu, K.; Asada, M. J. Antibiot. 2004, 57, 188. pmid: 21374771
	(b) Paterson, I.; Dalby, S. M.; Roberts, J. C.; Naylor, G. J.; Guzmán, E. A.; Isbrucker, R.; Pitts, T. P.; Linley, P.; Divlianska, D.; Reed, J. K.; Wright, A. E. Angew. Chem., Int. Ed. 2011, 50, 3219. doi: 10.1002/anie.201007719 pmid: 21374771
	(c) Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541. pmid: 21374771
[2]	(a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757. pmid: 11712502
	(b) Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853. pmid: 11712502
[3]	(a) Read, J. A.; Woerpel, K. A. J. Org. Chem. 2017, 82, 2300. pmid: 30081634
	(b) Bartolo, N. D.; Woerpel, K. A. J. Org. Chem. 2018, 83, 10197. doi: 10.1021/acs.joc.8b01430 pmid: 30081634
[4]	Cervera-Padrell, A. E.; Nielsen, J. P.; Pedersen, M. J.; Christensen, K. M.; Mortensen, A. R.; Skovby, T.; Dam-Johansen, K.; Kiil, S.; Gernaey, K. V. Org. Process Res. Dev. 2012, 16, 901.
[5]	Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536. pmid: 12047165
[6]	Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
[7]	Kanai, M.; Wada, P.; Shibuguchi, T.; Shibasaki, M. Pure Appl. Chem. 2008, 80, 1055.
[8]	Shi, S.-L.; Xu, L.-W.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 6638. doi: 10.1021/ja101948s pmid: 20420398
[9]	Motoki, R.; Tomita, D.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 8083.
[10]	Iwamoto, H.; Hayashi, Y.; Ozawa, Y.; Ito, H. ACS Catal. 2020, 10, 2471.
[11]	Zanghi, J. M.; Meek, S. J. Angew. Chem., Int. Ed. 2020, 59, 8451.
[12]	Sun, B.; Ruan, L.-X.; Zhao, R.; Zhang, J.; Niu, R.; Luo, Q.; Zhang, Y.; Gao, L.; Shi, S.-L. Nat. Synth. 2024, 3, 1091.
[13]	Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687.
[14]	Tsai, E. Y.; Liu, R. Y.; Yang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2018, 140, 2007.
[15]	Liu, R. Y.; Zhou, Y.; Yang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2019, 141, 2251.
[16]	Xu, M.; Lu, Q.; Gong, B.; Ti, W.; Lin, A.; Yao, H.; Gao, S. Angew. Chem., Int. Ed. 2023, 62, e202311540.
[17]	(a) Gupta, P.; Mahajan, N. New J. Chem. 2018, 42, 12296. pmid: 29805348
	(b) Mushtaq, S.; Abbasi, B. H.; Uzair, B.; Abbasi, R. EXCLI Journal 2018, 17, 420. doi: 10.17179/excli2018-1174 pmid: 29805348
[18]	Klake, R. K.; Edwards, M. D.; Sieber, J. D. Org. Lett. 2021, 23, 6444.
[19]	Collins, S.; Sieber, J. D. Org. Lett. 2023, 25, 1425.
[20]	Min, L.; Han, J.-C.; Zhang, W.; Gu, C.-C.; Zou, Y.-P.; Li, C.-C. Chem. Rev. 2023, 123, 4934.
[21]	Zhou, M.; Lin, Y.; Chen, X.-X.; Xu, G.; Chung, L. W.; Tang, W. Angew. Chem., Int. Ed. 2023, 62, e202300334.
[22]	Jiang, N.; Liu, P.-Z.; Pan, Z.-Z.; Wang, S.-Q.; Peng, Q.; Yin, L. Angew. Chem., Int. Ed. 2024, 63, e202402195.
[23]	Yang, Y.; Perry, I. B.; Lu, G.; Liu, P.; Buchwald, S. L. Science 2016, 353, 144. doi: 10.1126/science.aaf7720 pmid: 27284169
[24]	Li, C.; Liu, R. Y.; Jesikiewicz, L. T.; Yang, Y.; Liu, P.; Buchwald, S. L. J. Am. Chem. Soc. 2019, 141, 5062.
[25]	Fu, B.; Yuan, X.; Li, Y.; Wang, Y.; Zhang, Q.; Xiong, T.; Zhang, Q. Org. Lett. 2019, 21, 3576.
[26]	(a) McManus, H. A.; Fleming, M. J.; Lautens, M. Angew. Chem., Int. Ed. 2007, 46, 433. pmid: 7699710
	(b) Perrone, R.; Berardi, F.; Colabufo, N. A.; Leopoldo, M.; Tortorella, V.; Fiorentini, F.; Olgiati, V.; Ghiglieri, A.; Govoni, S. J. Med. Chem. 1995, 38, 942. pmid: 7699710
[27]	Acharyya, R. K.; Kim, S.; Park, Y.; Han, J. T.; Yun, J. Org. Lett. 2020, 22, 7897.
[28]	Zhu, J.; Rahim, F.; Zhou, P.; Zhang, A.; Malcolmson, S. J. J. Am. Chem. Soc. 2024, 146, 20270.
[29]	(a) Tewes, B.; Frehland, B.; Schepmann, D.; Robaa, D.; Uengwetwanit, T.; Gaube, F.; Winckler, T.; Sippl, W.; Wünsch, B. J. Med. Chem. 2015, 58, 6293.
	(b) Novoa, A.; Van Dorpe, S.; Wynendaele, E.; Spetea, M.; Bracke, N.; Stalmans, S.; Betti, C.; Chung, N. N.; Lemieux, C.; Zuegg, J.; Cooper, M. A.; Tourwé, D.; De Spiegeleer, B.; Schiller, P. W.; Ballet, S. J. Med. Chem. 2012, 55, 9549.
[30]	Li, D.; Park, Y.; Yoon, W.; Yun, H.; Yun, J. Org. Lett. 2019, 21, 9699.
[31]	Deng, X.-H.; Jiang, J.-X.; Jiang, Q.; Yang, T.; Chen, B.; He, L.; Chu, W.-D.; He, C.-Y.; Liu, Q.-Z. Org. Lett. 2022, 24, 4586.
[32]	Meng, F.; Jang, H.; Jung, B.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2013, 52, 5046.
[33]	Zhao, Y.-S.; Tang, X.-Q.; Tao, J.-C.; Tian, P.; Lin, G.-Q. Org. Biomol. Chem. 2016, 14, 4400.
[34]	(a) Yeung, K.; Talbot, F. J. T.; Howell, G. P.; Pulis, A. P.; Procter, D. J. ACS Catal. 2019, 9, 1655. doi: 10.1021/acscatal.8b04563
	(b) Deng, H.; Dong, Y.; Yu, S.; Yang, F.; Han, S.; Wu, J.; Liang, B.; Guo, H.; Zhang, C. Org. Lett. 2021, 23, 4431.
	(c) Ashraf, M. A.; Tambe, S. D.; Cho, E. J. Bull. Korean Chem. Soc. 2021, 42, 683.
[35]	Jang, H.; Romiti, F.; Torker, S.; Hoveyda, A. H. Nat. Chem. 2017, 9, 1269.
[36]	Zhao, C.-Y.; Zheng, H.; Ji, D.-W.; Min, X.-T.; Hu, Y.-C.; Chen, Q.-A. Cell Rep. Phys. Sci. 2020, 1, 100067.
[37]	Liu, X.; Shi, S. Chin. J. Org. Chem. 2024, 44, 1884.
[38]	Feng, J.-J.; Xu, Y.; Oestreich, M. Chem. Sci. 2019, 10, 9679.
[39]	Yoon, W. S.; Han, J. T.; Yun, J. Adv. Synth. Catal. 2021, 363, 4953.
[40]	Li, D.; Park, Y.; Yun, J. Org. Lett. 2018, 20, 7526.
[41]	Yazaki, R.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 5522. doi: 10.1021/ja101687p pmid: 20337453
[42]	Wei, X.-F.; Xie, X.-W.; Shimizu, Y.; Kanai, M. J. Am. Chem. Soc. 2017, 139, 4647.
[43]	Zhong, F.; Pan, Z.-Z.; Zhou, S.-W.; Zhang, H.-J.; Yin, L. J. Am. Chem. Soc. 2021, 143, 4556. doi: 10.1021/jacs.1c02084 pmid: 33734679
[44]	Liu, J.; Su, B.; Chen, M. Org. Lett. 2021, 23, 6035.
[45]	Pan, Z.-Z.; Li, J.-H.; Tian, H.; Yin, L. Angew. Chem., Int. Ed. 2024, 63, e202315293.
[46]	Pan, Z.-Z.; Pan, D.; Li, J.-H.; Xue, X.-S.; Yin, L. J. Am. Chem. Soc. 2023, 145, 1749.
[47]	(a) Fu, Z.; Xu, J.; Zhu, T.; Leong, W. W. Y.; Chi, Y. R. Nat. Chem. 2013, 5, 835.
	(b) Xie, Y.; Yu, C.; Li, T.; Tu, S.; Yao, C. Chem. Eur. J. 2015, 21, 5355.
	(c) Ma, J.; Rosales, A. R.; Huang, X.; Harms, K.; Riedel, R.; Wiest, O.; Meggers, E. J. Am. Chem. Soc. 2017, 139, 17245.

一价铜催化的酮或酮亚胺的不对称烯丙基化反应研究进展