Recent Progress in Applications of Cinchona Alkaloids and Their Derivatives in Asymmetric Catalysis
- Corresponding author: Chen Jiarong, chenjiarong@mail.ccnu.edu.cn Xiao Wenjing, wxiao@mail.ccnu.edu.cn
Citation: Xu Shuanghua, Chen Jun, Chen Jiarong, Xiao Wenjing. Recent Progress in Applications of Cinchona Alkaloids and Their Derivatives in Asymmetric Catalysis[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3493-3516. doi: 10.6023/cjoc202007004
Yang, F.; Hanon, S.; Lam, P.; Schweitzer, P. Am. J. Med. 2009, 122, 317.
doi: 10.1016/j.amjmed.2008.11.019
Haas, L. F. J. Neurol., Neurosurg. Psychiatry 1994, 57, 1333.
doi: 10.1136/jnnp.57.11.1333
Rabe, P.; Ackerman, E.; Schneider, W. Chem. Ber. 1907, 40, 3655.
doi: 10.1002/cber.190704003157
Woodward, R. B.; Doering, W. E. J. Am. Chem. Soc. 1945, 67, 860.
doi: 10.1021/ja01221a051
Carter, O. L.; McPhail, A. T.; Sim, G. A. J. Chem. Soc. A 1967, 365.
Stork, G.; Niu, D.; Fujimoto, R. A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239.
doi: 10.1021/ja004325r
Yeboah, E. O.; Yeboah, S.; Singh, G. Tetrahedron 2011, 67, 1725.
doi: 10.1016/j.tet.2010.12.050
Boratyński, P. J.; Błajet, M. Z; Skarżewsk, J. Textbook of The Alkaloids:Chemistry and Biology, Elsevier, Poland, 2019, p. 29.
List, B. Angew. Chem., Int. Ed. 2010, 49, 1730.
doi: 10.1002/anie.200906900
MacMillan, D. W. C. Nature 2008, 455, 304.
doi: 10.1038/nature07367
(a) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961.
(b) Tian, S. K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
(c) Singh, G.; Yeboah, E. Rep. Org. Chem. 2016, 6, 47.
Shi, L. M.; Dong, W. W.; Tao, H. Y.; Dong, X. Q.; Wang, C. J. Org. Lett. 2017, 19, 4532.
doi: 10.1021/acs.orglett.7b02107
Shao, Y. D.; He, X. Y.; Han, D. D.; Yang, X. R.; Yao, H. B.; Cheng, D. J. Asian J. Org. Chem. 2019, 8, 2023.
doi: 10.1002/ajoc.201900504
Mukhopadhyay, S.; Pan, S. C. Eur. J. Org. Chem. 2019, 2639.
Nakamura, S.; Hayama, D.; Miura, M.; Hatanaka, T.; Funahashi, Y. Org. Lett. 2018, 20, 856.
doi: 10.1021/acs.orglett.7b04022
Takata, S.; Endo, Y.; Ullah, M. S.; Itsuno, S. RSC Adv. 2016, 6, 72300.
doi: 10.1039/C6RA14535C
Endo, Y.; Takata, S.; Kumpuga, B. T.; Itsuno, S. ChemistrySelect 2017, 2, 10107.
doi: 10.1002/slct.201702010
Reddy, R. R.; Gudup, S. S.; Ghora, P. Angew. Chem. Int. Ed. 2016, 55, 15115.
doi: 10.1002/anie.201607039
Mondal, K.; Pan, S. C. J. Org. Chem. 2018, 83, 5301.
doi: 10.1021/acs.joc.8b00436
Wu, Y. C.; Jhong, Y.; Lin, H. J.; Swain, S. P.; Tsaia, H. H. G.; Hou, D. R. Adv. Synth. Catal. 2019, 361, 4966.
doi: 10.1002/adsc.201900997
Jiang, H. Y.; Li, Q.; Qi, Q. J.; Yang, C. X.; Zhang, D. Chin. J. Org. Chem. 2018, 38, 825(in Chinese).
Zhu, W.-R.; Liu, K.; Huang, W.-H.; Huang, W.-J.; Chen, Q.; Weng, J.; Lin, N.; Lu, G. Org. Lett. 2020, 22, 5014.
doi: 10.1021/acs.orglett.0c01578
Zi, Y.; Lange, M.; Schultz, C.; Vilotijevic, I. Angew. Chem. Int. Ed. 2019, 58, 10727.
doi: 10.1002/anie.201903392
Breman, A. C.; Heijden, G. V. D.; Maarseveen, J. H. V.; Ingemann, S.; Hiemstra, H. Chem. Eur. J. 2016, 22, 14247.
doi: 10.1002/chem.201601917
Kumpuga, B. T.; Itsuno, S. Asian J. Org. Chem. 2019, 8, 251.
doi: 10.1002/ajoc.201800740
Tichá, I. C.; Hybelbauerová, S.; Jindřich, J. J. Org. Chem. 2019, 15, 830.
Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
doi: 10.1021/cr00032a009
Yang, F.; Zhao, D. B.; Lan, J. B.; Xi, P. H.; Yang, L.; Xiang, S. H.; You, J. S. Angew. Chem. Int. Ed. 2008, 47, 5646.
doi: 10.1002/anie.200801766
Wang, J.; Wang, W. T.; Li, W.; Hu, X. L.; Shen, K.; Tan, C, ; Liu, X. H.; Feng, X. M. Chem. Eur. J. 2009, 15, 11642.
doi: 10.1002/chem.200900936
Su, Z. S.; Li, W. Y.; Wang, J.; Hu, C. W.; Feng, X. M. Chem. Eur. J. 2013, 19, 1637.
doi: 10.1002/chem.201202237
Wang, W. T.; Shen, K.; Hu, X. L.; Wang, J.; Liu, X. H.; Feng, X. M. Synlett 2009, 1655.
Wang, J.; Li, W.; Liu, Y. L.; Chu, Y. Y.; Lin, L. L.; Liu, X. H.; Feng, X. M. Org. Lett. 2010, 12, 1280.
doi: 10.1021/ol100169r
Shi, J.; Wang, M.; He, L.; Zheng, K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Chem. Commun. 2009, 31, 4711.
Richter, C.; Ranganath, K. V. S.; Glorius, F. Adv. Synth. Catal. 2012, 354, 377.
doi: 10.1002/adsc.201100669
Hartikka, A.; Modin, S. A.; Arvidsson, P. G. Org. Biomol. Chem. 2003, 1, 2522.
doi: 10.1039/b304060g
He, W.; Liu, P.; Zhang, B. L.; Sun, X. L.; Zhang, S. Y. Appl. Organomet. Chem. 2006, 20, 328.
doi: 10.1002/aoc.1055
Hayashi, M.; Shiomi, N.; Funahashi, Y.; Nakamura, S. J. Am. Chem. Soc. 2012, 134, 19366.
doi: 10.1021/ja309963w
Hayashi, M.; Iwanaga, M.; Shiomi, N.; Nakane, D.; Masuda, H.; Nakamura, S. Angew. Chem. Int. Ed. 2014, 53, 8411.
doi: 10.1002/anie.201404629
Yamaji, R.; Iwanaga, M.; Nakamura, S. Chem. Commun. 2016, 52, 7462.
doi: 10.1039/C6CC02911F
Shen, B.; Huang, H. Y.; Bian, G. L.; Zong, H.; Song, L. Chirality 2013, 25, 561.
doi: 10.1002/chir.22171
Liu, M.; Ma, S. J.; Tian, Z. Q.; Wu, H.; Wu, L. L.; Xu, X. F.; Huang, Y. D.; Wang, Y. M. Tetrahedron:Asymmetry 2013, 24, 736.
doi: 10.1016/j.tetasy.2013.05.009
Li, X. T.; Gu, Q. S.; Dong, X. Y.; Meng, X.; Liu, X. Y. Angew. Chem. Int. Ed. 2018, 57, 7668.
doi: 10.1002/anie.201804315
Li, X. T.; Lv, L.; Wang, T.; Zhang, X. H.; Cheng, G. J.; Liu, X. Y. Chem 2020, 6, 1692.
doi: 10.1016/j.chempr.2020.03.024
Tian, Q. Q.; Liu, Y. L.; Wang, X. Y.; Wang, X.; He, W. Eur. J. Org. Chem. 2019, 24, 3850.
Zielińska, B. M.; Skarżewski, J. Tetrahedron:Asymmetry 2009, 20, 1992.
doi: 10.1016/j.tetasy.2009.07.020
Wei, Y.; Yao, L.; Zhang, B. L.; He, W.; Zhang, S. Y. Tetrahedron 2011, 67, 8552.
doi: 10.1016/j.tet.2011.08.076
Wang, Q. F.; He, W.; Liu, X. Y.; Chen, H.; Qin, X. Y.; Zhang, S. Y. Tetrahedron:Asymmetry 2008, 19, 2447.
doi: 10.1016/j.tetasy.2008.10.030
Sladojevich, F.; Trabocchi, A.; Guarna, A.; Dixon, D. J. J. Am. Chem. Soc. 2011, 133, 1710.
doi: 10.1021/ja110534g
Campa, R.; Dixon, D. J. Angew. Chem. Int. Ed. 2015, 54, 4895.
doi: 10.1002/anie.201411852
Ortin, I.; Dixon, D. J. Angew. Chem. Int. Ed. 2014, 53, 3462.
doi: 10.1002/anie.201309719
Campa, R.; Yamagata, A. D. G.; Ortin, I, Franchino, A.; Thompson, A. L.; Odell, B.; Dixon, D. J. Chem. Commun. 2016, 52, 10632.
doi: 10.1039/C6CC04132A
Manzano, R.; Rubén; Datta, S.; Paton, R.; Dixon, D. J. Angew. Chem. Int. Ed. 2017, 56, 5834.
doi: 10.1002/anie.201612048
Zheng, S. C.; Wang, Q.; Zhu, J. P. Angew. Chem. Int. Ed. 2019, 58, 1494.
doi: 10.1002/anie.201812654
Casarotto, V.; Li, Z. T.; Boucau, J.; Lin, Y. M. Tetrahedron. Lett. 2007, 48, 5561.
doi: 10.1016/j.tetlet.2007.05.130
Yao, L.; Wei, Y.; Wang, P. G.; He, W.; Zhang, S. Y. Tetrahedron 2012, 68, 9119.
doi: 10.1016/j.tet.2012.08.029
Dong, X. Y.; Zhang, Y. F.; Ma, C. L, ; Gu, Q. S.; Wang, F. L.; Li, Z. L.; Jiang, S. P.; Liu, X. Y. Nat. Chem. 2019, 11, 1158.
doi: 10.1038/s41557-019-0346-2
Xia, H. D.; Li, Z. L.; Gu, Q. S.; Dong, X. Y.; Fang, J. H.; Du, X. Y.; Wang, L. L.; Liu, X. Y. Angew. Chem. Int. Ed. 2020, 59, 16926.
doi: 10.1002/anie.202006317
Zhang, Z. H.; Dong, X. Y.; Du, X. Y.; Gu, Q. S.; Li, Z. L.; Liu, X. Y. Nat. Commun. 2019, 10, 5689.
doi: 10.1038/s41467-019-13705-1
Dong, X.-Y.; Cheng, J.-T.; Zhang, Y.-F.; Li, Z.-L.; Zhan, T.-Y.; Chen, J.-J.; Wang, F.-L.; Yang, N.-Y.; Ye, L.; Gu, Q.-S.; Liu, X.-Y. J. Am. Chem. Soc. 2020, 142, 9501.
doi: 10.1021/jacs.0c03130
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