Chinese Journal of Organic Chemistry >
Research Progress of Copper-Catalyzed Direct Vinylogous Reactions
Received date: 2022-01-20
Revised date: 2022-02-25
Online published: 2022-03-08
Supported by
Grants from the Shanxi Scholarship Council of China(2020-141); Key R & D Program of Shanxi Province(201903D121105); National Natural Science Foundation of China(21871287); National Natural Science Foundation of China(21922114); Science and Technology Commission of Shanghai Municipality(20JC1417100); Science and Technology Commission of Shanghai Municipality(21XD1424800)
Vinylogous reaction serves as an efficient tool to introduce a new functional group at the γ-position (or even more remote position) of the parent functional group. The produced highly functionalized structure motifs (especially chiral ones) are ubiquitous in natural products, biologically active compounds and pharmaceuticals. Moreover, they work as important synthetic intermediates in organic syntheses. Therefore, asymmetric vinylogous reaction has gained extensive attention in recent years. Our group is interested in the development of efficient direct vinylogous reactions by using copper catalysts with a focus on the catalytic asymmetric variants. Herein, the advances in our group in this field are reviewed. Both α,β-unsaturated and β,γ-unsaturated compounds (including esters, aldehydes, ketones, phosphonates, sulfones, and nitriles) are used as the vinylogous pronucleophiles. Aldehydes, ketones, imines, and molecular oxygen are employed as the electrophiles. This account is divided into three sections based on the varied electrophiles: asymmetric vinylogous aldol reaction, asymmetric vinylogous Mannich reaction and vinylogous aerobic oxidative hydroxylation. By using suitable copper catalysts, these reactions generally afforded the vinylogous products in good to excellent yields with good to excellent control of regio-, diastereo-, and enantioselectivities.
Hui Li , Liang Yin . Research Progress of Copper-Catalyzed Direct Vinylogous Reactions[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1573 -1585 . DOI: 10.6023/cjoc202201033
| [1] | Fuson, R. C. Chem. Rev. 1935, 16, 1. |
| [2] | For selective reviews, see: (a) Denmark, S. E.; Heemstra, J. R.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682. |
| [2] | (b) Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076. |
| [2] | (c) Pansare, S.V.; Paul, E. K. Chem.-Eur. J. 2011, 17, 8770. |
| [2] | (d) Bisai, V. Synthesis 2012, 44, 1453. |
| [2] | (e) Schneider, C.; Abels, F. Org. Biomol. Chem. 2014, 12, 3531. |
| [2] | (f) Jusseau, X.; Chabaud, L.; Guillou, C. Tetrahedron 2014, 70, 2595. |
| [2] | (g) Roselló, M. S.; Pozo, C. D.; Fustero, S. Synthesis 2016, 48, 2553. |
| [2] | (h) Yin, Y.; Jiang, Z. ChemCatChem 2017, 9, 4306. |
| [2] | (i) Li, H.; Yin, L. Tetrahedron Lett. 2018, 59, 4121. |
| [2] | (j) Li, Z.; Noda, H.; Kumagai, N.; Shibasaki, M. Tetrahedron 2018, 74, 3301. |
| [3] | For some recent examples for transition-metal-catalyzed asymmetric vinylogous reaction, see: (a) Tang, Q.; Lin, L.; Ji, J.; Hu, H.; Liu, X.; Feng, X. Chem.-Eur. J. 2017, 23, 16447. |
| [3] | (b) Trost, B. M.; Gnanamani, E.; Tracy, J. S.; Kalnmals, C. A. J. Am. Chem. Soc. 2017, 139, 18198. |
| [3] | (c) Ji, J.; Lin, L.; Tang, Q.; Kang, T.; Liu, X.; Feng, X. ACS Catal. 2017, 7, 3763. |
| [3] | (d) Mei, H.; Lin, L.; Wang, L.; Dai, L.; Liu, X.; Feng, X. Chem. Commun. 2017, 53, 8763. |
| [3] | (e) Sarkar, R.; Mitra, S.; Mukherjee, S. Chem. Sci. 2018, 9, 5767. |
| [3] | (f) Shi, C.-Y.; Xiao, J.-L.; Yin, L. Chem. Commun. 2018, 54, 11957. |
| [3] | (g) Xu, H.; Laraia, L.; Schneider, L.; Louven, K.; Strohmann, C.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2017, 56, 11232. |
| [4] | For some recent examples for organocatalyzed asymmetric vinylogous reaction, see: (a) Han, J.-L.; Tsai, Y.-D.; Chang, C.-H. Adv. Synth. Catal. 2017, 359, 4043. |
| [4] | (b) Sakai, T.; Hirashima, S.; Yamashita, Y.; Arai, R.; Nakashima, K.; Yoshida, A.; Koseki, Y.; Miura, T. J. Org. Chem. 2017, 82, 4661. |
| [4] | (c) Kumar, K.; Jaiswal, M. K.; Singh, R. P. Adv. Synth. Catal. 2017, 359, 4136. |
| [4] | (d) Han, M.-Y.; Luan, W.-Y.; Mai, P.-L.; Li, P.; Wang, L. J. Org. Chem. 2018, 83, 1518. |
| [4] | (e) Bai, X.; Zeng, G.; Shao, T.; Jiang, Z. Angew. Chem., Int. Ed. 2017, 56, 3684. |
| [4] | (f) Rout, S.; Joshi, H.; Singh, V. K. Org. Lett. 2018, 20, 2199. |
| [4] | (g) Arlt, A.; Toyama, H.; Takada, K.; Hashimoto, T.; Maruoka, K. Chem. Commun. 2017, 53, 4779. |
| [4] | (h) Silva, S.; Matsuo, B. T.; da Silva, R. C.; Pozzi, L. V.; Correa, A. G.; Rollin, P.; Zukerman-Schpector, J.; Ferreira, M. A. B.; Paixão, M. W. J. Org. Chem. 2018, 83, 1701. |
| [5] | Curti, C.; Brindani, N.; Battistini, L.; Sartori, A.; Pelosi, G.; Mena, P.; Brighenti, F.; Zanardi, F.; Del Rio, D. Adv. Synth. Catal. 2015, 357, 4082. |
| [6] | Denmark, S. E.; Heemstra, J. R.,Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682. |
| [7] | (a) Cui, J.; Ohtsuki, A.; Watanabe, T.; Kumagai, N.; Shibasaki, M. Chem.-Eur. J. 2018, 24, 2598. |
| [7] | (b) Takeuchi, T.; Kumagai, N.; Shibasaki, M. J. Org. Chem. 2018, 83, 5851. |
| [8] | Jing, Z.; Bai, X.; Chen, W.; Zhang, G.; Zhu, B.; Jiang, Z. Org. Lett. 2016, 18, 260. |
| [9] | Boucard, V.; Broustal, G.; Campagne, J. M. Eur. J. Org. Chem. 2007, 2007, 225. |
| [10] | Zhang, H.-J.; Yin, L. J. Am. Chem. Soc. 2018, 140, 12270. |
| [11] | (a) Yuan, C.; Yao, J.; Li, S. Phosphorus Sulfur Silicon Relat. Elem. 1990, 53, 21. |
| [11] | (b) Yuan, C.; Yao, J.; Li, S. Phosphorus Sulfur Silicon Relat. Elem. 1991, 55, 125. |
| [11] | (c) Kisanga, K.; Verkade, J. G. J. Org. Chem. 2002, 67, 426. |
| [11] | (d) Chinkov, N.; Majumdar, S.; Marek, I. J. Am. Chem. Soc. 2003, 125, 13258. |
| [12] | Yue, W.-J.; Zhang, C.-Y.; Yin, L. iScience 2019, 14, 88. |
| [13] | Narasimhulu, M.; Reddy, T. S.; Mahesh, K. C.; Krishna, A. S.; Rao, J. V.; Venkateswarlu, Y. Bioorg. Med. Chem. Lett. 2009, 19, 3125. |
| [14] | Rivera-Fuentes, P.; Diederich, F. Angew. Chem., Int. Ed. 2012, 51, 2818. |
| [15] | (a) Zimmer, R.; Reissig, H.-U. Chem. Soc. Rev. 2014, 43, 2888. |
| [15] | (b) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927. |
| [16] | (a) Pu, X.; Qi, X.; Ready, J. M. J. Am. Chem. Soc. 2009, 131, 10364. |
| [16] | (b) Cai, F.; Pu, X.; Qi, X.; Lynch, V.; Radha, A.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 18066. |
| [17] | (a) Zhong, F.; Xue, Q.-Y.; Yin, L. Angew. Chem., Int. Ed. 2020, 59, 1562. |
| [17] | (b) Ran, G.; Chen, Y. Chin. J. Org. Chem. 2020, 40, 814. (in Chinese) |
| [17] | ( 冉光尧, 陈应春, 有机化学, 2020, 40, 814.) |
| [18] | Ran, G.-Y.; Chen, C.; Yang, X.-X.; Zhao, Z.; Du, W.; Chen, Y.-C. Org. Lett. 2020, 22, 4732. |
| [19] | Bai, X.; Zeng, G.; Shao, T.; Jiang, Z. Angew. Chem., Int. Ed. 2017, 56, 3684. |
| [20] | Wang, S.-Q.; Liu, Z.-C.; Yue, W.-J.; Yin, L. Angew. Chem., Int. Ed. 2021, 60, 4604. |
| [21] | Wei, X.-F.; Xie, X.-W.; Shimizu, Y.; Kanai, M. J. Am. Chem. Soc. 2017, 139, 4647. |
| [22] | (a) Zhong, F.; Pan, Z.-Z.; Zhou, S.-W.; Zhang, H.-J.; Yin, L. J. Am. Chem. Soc. 2021, 143, 4556. |
| [22] | (b) Gu, X.; Xu, L. Chin. J. Org. Chem. 2021, 41, 2528. (in Chinese) |
| [22] | ( 顾幸威, 徐利文, 有机化学, 2021, 41, 2528.) |
| [23] | Ruan, S.-T.; Luo, J.-M.; Du, Y.; Huang, P.-Q. Org. Lett. 2011, 13, 4938. |
| [24] | Trost, B. M.; Gnanamani, E.; Tracy, J. S.; Kalnmals, C. A. J. Am. Chem. Soc. 2017, 139, 18198. |
| [25] | Zhang, H.-J.; Shi, C.-Y.; Zhong, F.; Yin, L. J. Am. Chem. Soc. 2017, 139, 2196. |
| [26] | (a) Zhou, Z.; Feng, X.; Yin, X.; Chen, Y.-C. Org. Lett. 2014, 16, 2370. |
| [26] | (b) Dell’Amico, L.; Rassu, G.; Zambrano, V.; Sartori, A.; Curti, C.; Battistini, L.; Pelosi, G.; Casiraghi, G.; Zanardi, F. J. Am. Chem. Soc. 2014, 136, 11107. |
| [26] | (c) Ratjen, L.; García-García, P.; Lay, F.; Beck, M. E.; List, B. Angew. Chem., Int. Ed. 2011, 50, 754. |
| [27] | Zhong, F.; Yue, W.-J.; Zhang, H.-J.; Zhang, C.-Y.; Yin, L. J. Am. Chem. Soc. 2018, 140, 15170. |
| [28] | Gribble, G. W. Environ. Chem. 2015, 12, 396. |
| [29] | Zhang, H.-J.; Zhong, F.; Xie, Y.-C.; Yin, L. Chin. J. Chem. 2021, 39, 55. |
| [30] | (a) Shiina, I.; Takasuna, Y.; Suzuki, R.; Oshiumi, H.; Komiyama, Y.; Hitomi, S.; Fukui, H. Org. Lett. 2006, 8, 5279. |
| [30] | (b) Fukui, H.; Shiina, I. Org. Lett. 2008, 10, 3153. |
| [31] | Keeri, A. R.; Gualandi, A.; Mazzanti, A.; Lewinski, J.; Cozzi, P. G. Chem.-Eur. J. 2015, 21, 18949. |
| [32] | (a) Arai, T.; Sato, T.; Noguchi, H.; Kanoh, H.; Kaneko, K.; Yanagisawa, A. Chem. Lett. 2006, 35, 1094. |
| [32] | (b) Tsang, A. S.-K.; Kapat, A.; Schoenebeck, F. J. Am. Chem. Soc. 2016, 138, 518. |
| [33] | Zhang, H.-J.; Schuppe, A. W.; Pan, S.-T.; Chen, J.-X.; Wang, B.-R.; Newhouse, T. R.; Yin, L. J. Am. Chem. Soc. 2018, 140, 5300. |
/
| 〈 |
|
〉 |
