SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 2: 284 - 299

DOI: https://doi.org/10.6023/cjoc201909028

Advances in Multicomponent Asymmetric Cascade Synthesis Involving Nitroolefin Catalyzed by Diarylprolinol Derivatives

  • Yan Lijun ,
  • Xu Han ,
  • Wang Yan ,
  • Dong Jianwei ,
  • Wang Yongchao
Expand
  • a College of Vocational and Technical Education, Yunnan Normal University, Kunming 650092;
    b College of Chemistry and Environmental Science, Qujing Normal University, Qujing, Yunnan 655011

Received date: 2019-09-17

  Revised date: 2019-10-28

  Online published: 2019-12-19

Supported by

Project supported by the Applied Basic Research Project of Yunnan Provincial Department of Science and Technology (Nos. 2017FD073, 2018FD016, 2018FD081), the Scientific Research Foundation of Yunnan Provincial Education Department (No. 2017ZZX075) and the Yunnan Local Colleges Applied Basic Research Project (No. 2017FH001-092).

Fold

Abstract

Nitroolefin is an important class of organic synthons. The synthetic method of multicomponent asymmetric cascade reactions involving nitroolefin catalyzed by diarlyprolinol derivatives is quite important for the construction of complex chiral compounds. It is widely used in organic synthesis and new drugs development. In this paper, the multi-component asymmetric cascade synthesis involving nitroalkenes catalyzed by diarlyprolinol derivatives is comprehensively summarized based on the type of target compounds. In detail, the catalyst systems, reaction mechanisms, experimental results, reaction advantages, existing problems and limitations for this synthetic method are introduced respectively. The future development for this synthetic period is further evaluated as well.

Key words： nitroolefin; diarlyprolinol derivatives; multicomponent reactions; asymmetric synthesis; cascade reactions

Cite this article

Yan Lijun , Xu Han , Wang Yan , Dong Jianwei , Wang Yongchao . Advances in Multicomponent Asymmetric Cascade Synthesis Involving Nitroolefin Catalyzed by Diarylprolinol Derivatives[J]. Chinese Journal of Organic Chemistry, 2020 , 40(2) : 284 -299 . DOI: 10.6023/cjoc201909028

References

[1] (a) Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev. 2014, 114, 2390.
(b) Carlone, A.; Cabrera, S.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101.
(c) Enders, D.; Grondal, C.; Huettl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
(d) Chauhan, P.; Mahajan, S.; Kaya, U.; Hack, D.; Enders, D. Adv. Synth. Catal. 2015, 357, 253.
(e) Yan, L. J.; Wang, Y. C. ChemistrySelect 2016, 1, 6948.
(f) Su, Y.; Bouma, M. J.; Alcaraz, L.; Stocks, M.; Furber, M.; Masson, G.; Zhu, J. Chem.-Eur. J. 2012, 18, 12624.
(g) Han, Z. Y.; Gong, L. Z. Prog. Chem. 2018, 30, 505(in Chinese). (韩志勇, 龚流柱, 化学进展, 2018, 30, 505.)
[2] (a) Cao, Y.; Jiang, X.; Liu, L.; Shen, F.; Zhang, F.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 9124.
(b) Chi, Y.; Scroggins, S. T.; Fréchet, J. M. J. J. Am. Chem. Soc. 2008, 130, 6322.
(c) Enders, D.; Huettl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861.
(d) Blümel, M.; Chauhan, P.; Hahn, R.; Raabe, G.; Enders, D. Org. Lett. 2014, 16, 6012.
(e) Liao, X.; Jiang, Y.; Lai, S. L.; Liu, Y. G.; Wang, S. B.; Xiong, X. Q. Chin. J. Org. Chem. 2019, 39, 668(in Chinese). (廖旭, 蒋岩, 赖石林, 刘源岗, 王士斌, 熊兴泉, 有机化学, 2019, 39, 668.)
[3] (a) Yu, X.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037.
(b) Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167.
(c) Jia, Z.-J.; Jiang, H.; Li, J.-L.; Gschwend, B.; Li, Q.-Z.; Yin, X.; Grouleff, J.; Chen, Y.-C.; Jørgensen, K. A. J. Am. Chem. Soc. 2011, 133, 5053.
(d) Zu, L.; Xie, H.; Li, H.; Wang, J.; Yu, X.; Wang, W. Chem.-Eur. J. 2008, 14, 6333.
[4] (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. 1971, 10, 496.
(b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
[5] Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794.
[6] Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
[7] (a) Rueping, M.; Kuenkel, A.; Tato, F.; Bats, J. W. Angew. Chem., Int. Ed. 2009, 48, 3699.
(b) Silvi, M.; Chatterjee, I.; Liu, Y.; Melchiorre, P. Angew. Chem., Int. Ed. 2013, 52, 10780.
(c) Ma, A.; Ma, D. Org. Lett. 2010, 12, 3634.
(d) Johansen, T. K.; Gómez, C. V.; Bak, J. R.; Davis, R. L.; Jørgensen, K. A. Chem.-Eur. J. 2013, 19, 16518.
(e) Talavera, G.; Reyes, E.; Vicario, J. L.; Carrillo, L. Angew. Chem., Int. Ed. 2012, 51, 4104.
(f) Li, J. L.; Zhou, S. L.; Chen, P. Q.; Dong, L.; Liu, T. Y.; Chen, Y. C. Chem. Sci. 2012, 3, 1879.
[8] (a) Barrett, A. G.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
(b) Yoshikoshi, A.; Miyashita, M. Acc. Chem. Res. 1985, 18, 284.
(c) Zimmer, R.; Reissig, H. U. Chem. Soc. Rev. 2014, 43, 2888.
[9] (a) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316.
(b) Rao, P. S.; Kurumurthy, C.; Veeraswamy, B.; Kumar, G. S.; Poornachandra, Y.; Kumar, C. G.; Vasamsetti, S. B.; Kotamraju, S.; Narsaiah, B. Eur. J. Med. Chem. 2014, 80, 184.
(c) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865.
(d) Zhang, W. S.; Xu, W. J.; Zhang, F.; Li, Y. Chin. J. Org. Chem. 2019, 39, 1277(in Chinese). (张文生, 许文静, 张斐, 李焱, 有机化学, 2019, 39, 1277.)
[10] (a) Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415.
(b) Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023.
(c) Wang, Y.-C.; Wang, J.-L.; Burgess, K. S.; Zhang, J.-W.; Zheng, Q.-M.; Pu, Y.-D.; Yan, L.-J.; Chen, X.-B. RSC Adv. 2018, 8, 5702.
(d) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666.
(e) Liao, F. M.; Du, Y.; Zhou, F.; Zhou, J. Acta Chim. Sinica 2018, 76, 862(in Chinese). (廖富民, 杜溢, 周锋, 周剑, 化学学报, 2018, 76, 862.)
[11] (a) Zhao, Y.; Yu, S.; Sun, W.; Liu, L.; Lu, J.; McEachern, D.; Shargary, S.; Bernard, D.; Li. X.; Zhao, T.; Zou, P.; Sun, D.; Wang, S. J. Med. Chem. 2013, 56, 5553.
(b) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.;Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. J. Am. Chem. Soc. 2005, 127, 10130.
(c) Kumari, G.; Modi, M.; Gupta, S. K.; Singh, R. K. Eur. J. Med. Chem. 2011, 46, 1181.
(d) Arun, Y.; Saranraj, K.; Balachandran, C.; Perumal, P. T. Eur. J. Med. Chem. 2014, 74, 50.
(e) Kathirvelan, D.; Haribabu, J.; Reddy, B. S. R.; Balachandran, C.; Duraipandiyan, V. Bioorg. Med. Chem. Lett. 2015, 25, 389.
[12] (a) Cheng, D.; Ishihara, Y.; Tan, B.; Barbas III, C. F. ACS Catal. 2014, 4, 743.
(b) Tian, L.; Luo, Y. C.; Hu, X. Q.; Xu, P. F. Asian J. Org. Chem. 2016, 5, 580.
(c) Mei, G. J.; Shi, F. Chem. Commun. 2018, 54, 6607.
(d) Fang, X.; Wang, C.-J. Org. Biomol. Chem. 2018, 16, 2591.
[13] Jiang, K.; Jia, Z.-J.; Chen, S.; Wu, L.; Chen, Y.-C. Chem.-Eur. J. 2010, 16, 2852.
[14] Jiang, K.; Jia, Z.-J.; Yin, X.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 2766.
[15] Xie, X.; Peng, C.; He, G.; Leng, H. J.; Wang, B.; Huang, W.; Han, B. Chem. Commun. 2012, 48, 10487.
[16] Zhou, B.; Yang, Y.; Shi, J.; Luo, Z.; Li, Y. J. Org. Chem. 2013, 78, 2897.
[17] Li, Z.-L.; Liu, C.; Tan, R.; Tong, Z.-P.; Liu, Y.-K. Catalysts 2016, 6, 65.
[18] Chaudhari, P. D.; Hong, B. C.; Lee, G. H. Org. Lett. 2017, 19, 6112.
[19] (a) Rajapaksa, N. S.; McGowan, M. A.; Rienzo, M.; Jacobsen, E. N. Org. Lett. 2013, 15, 706.
(b) Granger, B. A.; Wang, Z.; Kaneda, K.; Fang, Z.; Martin, S. F. ACS Comb. Sci. 2013, 15, 379.
(c) Dounay, A. B.; Humphreys, P. G.; Overman, L. E.; Wrobleski, A. D. J. Am. Chem. Soc. 2008, 130, 5368.
(d) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
[20] Tan, Y.; Luan, H. L.; Lin, H.; Sun, X. W.; Yang, X. D.; Dong, H. Q.; Lin, G. Q. Chem. Commun. 2014, 50, 10027.
[21] Enders, D.; Wang, C.; Mukanova, M.; Greb, A. Chem. Commun. 2010, 46, 2447.
[22] (a) Karasu, S.; Bayram, Y.; Ozkan, K.; Sagdic, O. J. Food Meas. Charact. 2019, 13, 1515.
(b) Wu, X.; Yang, S.; Yu, H.; Ye, L.; Su, B.; Shao, Z. Biosci. Biotechnol. Biochem. 2019, 83, 1263.
[23] Enders, D.; Hüttl, M. R. M.; Raabe, G.; Bats, J. W. Adv. Synth. Catal. 2008, 350, 267.
[24] Enders, D.; Hüttl, M. R. M.; Runsink, J.; Raabe, G.; Wendt, B. Angew. Chem., Int. Ed. 2007, 46, 467.
[25] Zhang, F.-L.; Xu, A.-W.; Gong, Y.-F.; Wei, M.-H.; Yang, X.-L. Chem.-Eur. J. 2009, 15, 6815.
[26] Enders, D.; Krüell, R.; Bettray, W. Synthesis 2010, 567.
[27] Rueping, M.; Haack, K. L.; Ieawsuwan, W.; Sunden, H.;Blanco, M.; Schoepke, F. R. Chem. Commun. 2011, 47, 3828.
[28] Jia, Y.; Mao, Z.; Wang, R. Tetrahedron:Asymmetry 2011, 22, 2018.
[29] Erdmann, N.; Philipps, A. R.; Atodiresei, I.; Enders, D. Adv. Synth. Catal. 2013, 355, 847.
[30] Philipps, A. R.; Fritze, L.; Erdmann, N.; Enders, D. Synthesis 2015, 47, 2377.
[31] (a) Simon-Levert, A.; Arrault, A.; Bontemps-Subielos N;Canal, C.; Banaigs, B. J. Nat. Prod. 2005, 68, 1412.
(b) Pratap, R.; Ram, V. J. Chem. Rev. 2014, 114, 10476.
(c) Tangdenpaisal, K.; Chuayboonsong, K.; Ruchirawat, S.; Ploypradith, P. J. Org. Chem. 2017, 82, 2672.
(d) Garrido, L.; Zubia, E.; Ortega, M. J.; Salva, J. J. Nat. Prod. 2002, 65, 1328.
[32] Kotame, P.; Hong, B. C.; Liao, J.-H. Tetrahedron Lett. 2009, 50, 704.
[33] Hong, B.-C.; Kotame, P.; Tsai, C.-W.; Liao, J.-H. Org. Lett. 2010, 12, 776.
[34] Kumar, M.; Chauhan, P.; Valkonen, A.; Rissanen, K.; Enders, D. Org. Lett. 2017, 19, 3025.
[35] Kumar, M.; Chauhan, P.; Bailey, S. J.; Jafari, E.; von Essen, C.; Rissanen, K.; Enders, D. Org. Lett. 2018, 20, 1232.
[36] (a) Perreault, S.; Rovis, T. Chem. Soc. Rev. 2009, 38, 3149.
(b) Mengozzi, L.; Gualandi, A.; Cozzi, P. G. Chem. Sci. 2014, 5, 3915.
(c) Friedman, R. K.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10775.
(d) Eschenbrenner-Lux, V.; Küchler, P.; Ziegler, S.; Kumar, K.; Waldmann, H. Angew. Chem., Int. Ed. 2014, 53, 2134.
(e) Khashper, A.; Lubell, W. D. Org. Biomol. Chem. 2014, 12, 5052.
[37] (a) Hayashi, Y.; Gotoh, H.; Masui, R.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 4012.
(b) Han, B.; Li, J. L.; Ma, C.; Zhang, S. J.; Chen, Y. C. Angew. Chem., Int. Ed. 2008, 47, 9971.
(c) Han, B.; He, Z. Q.; Li, J. L.; Li, R.; Jiang, K.; Liu, T. Y.; Chen, Y. C. Angew. Chem., Int. Ed. 2009, 48, 5474.
[38] Wang, Y.; Yu, D.-F.; Liu, Y.-Z.; Wei, H.; Luo, Y.-C.; Dixon, D. J.; Xu, P.-F. Chem.-Eur. J. 2010, 16, 3922.
[39] Urushima, T.; Sakamoto, D.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2010, 12, 4588.
[40] Chawla, R.; Rai, A.; Singh, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2012, 53, 5323.
[41] Tan, Y.; Chen, Y. J.; Lin, H.; Luan, H. L.; Sun, X. W.; Yang, X. D.; Lin, G. Q. Chem. Commun. 2014, 50, 15913.
[42] (a) Kariba, R. M.; Houghton, P. J.; Yenesew, A. J. Nat. Prod. 2002, 65, 566.
(b) Hubbs, J. L.; Heathcock, C. H. Org. Lett. 1999, 1, 1315.
(c) Padwa, A.; Flick, A. C.; Lee, H. I. Org. Lett. 2005, 7, 2925.
(d) Zhou, J.; Magomedov, N. A. J. Org. Chem. 2007, 72, 3808.
(e) Wöfling, J.; Frank, É.; Schneider, G.; Bes, M. T.; Tietze, L. F. Synlett 1998, 1205.
(f) Mernyák, E.; Schneider, G.; Herbst-Irmer, R.; Kubas, M.; Wölfing, J. Steroids 2006, 71, 558.
[43] Rai, A.; Singh, A. K.; Singh, S.; Yadav, L. D. S. Synlett 2011, 335.
[44] Rai, A.; Singh, A. K.; Singh, P.; Yadav, L. D. S. Tetrahedron Lett. 2011, 52, 1354.
[45] Jensen, K. L.; Dickmeiss, G.; Donslund, B. S.; Poulsen, P. H.; Jørgensen, K. A. Org. Lett. 2011, 13, 3678.
[46] (a) Yeung, K.-S.; Paterson, I. Chem. Rev. 2005, 105, 4237.
(b) Nising, C. F.;Brase, S. Chem. Soc. Rev. 2012, 41, 988.
(c) Clarke, P. A., Santos S. Eur. J. Org. Chem. 2006, 2045.
(d) Larrosa, I.; Romea, P.; Urpí, F. Tetrahedron 2008, 64, 2683.
(e) Xiao, Y. Y.; Wang, Y. M.; Zhou, Z. H. Chin. J. Org. Chem. 2019, 39, 2203(in Chinese). (肖园园, 王有名, 周正洪, 有机化学, 2019, 39, 2203.)
[47] Ishikawa, H.; Sawano, S.; Yasui, Y.; Shibata, Y.; Hayashi, Y. Angew. Chem., Int. Ed. 2011, 50, 3774.
[48] Han, B.; Xie, X.; Huang, W.; Li, X.; Yang, L.; Peng, C. Adv. Synth. Catal. 2014, 356, 3676.
[49] (a) Okpekon, T.; Millot, M.; Champy, P.; Gleye, C.; Yolou, S.; Bories, C.; Loiseau, P.; Laurens, A.; Hocquemiller, R. Nat. Prod. Res. 2009, 23, 909.
(b) Seiser, T.; Cramer, N. Angew. Chem., Int. Ed. 2010, 49, 10163.
(c) Kim, S. H.; Kwon, S. H.; Park, S. H.; Lee, J. K.; Bang, H. S.; Nam, S. J.; Kwon, H. C.; Shin, J.; Oh, D. C. Org. Lett. 2013, 15, 1834.
(d) Yang, Y.; Philips, D.; Pan, S. J. Org. Chem. 2011, 76, 1902.
[50] Li, X.; Yang, L.; Peng, C.; Xie, X.; Leng, H.-J.; Wang, B.; Tang, Z.-W.; He, G.; Ouyang, L.; Huang, W.; Han, B. Chem. Commun. 2013, 49, 8692.
[51] Dochain, S.; Vetica, F.; Puttreddy, R.; Rissanen, K.; Enders, D. Angew. Chem. 2016, 128, 16387.
[52] (a) Gao, C.; Han, L.; Zheng, D.; Jin, H.; Gai, C.; Wang, J.; Zhang, H.; Zhang, L.; Fu, H. J. Nat. Prod. 2015, 78, 630.
(b) Lee, S. H.; Tanaka, T.; Nonaka, G. I.; Nishioka, I. J. Nat. Prod. 2004, 67, 1018.
(c) Vila, R.; Mundina, M.; Muschietti, L.; Priestap, H. A.; Bandoni, A. L.; Adzet, T.; Cañigueral, S. Phytochemistry 1997, 46,1127.
[53] (a) Nagata, H.; Inagaki, Y.; Tanaka, M.; Ojima, M.; Kataoka, K.; Kuboniwa, M.; Nishida, N.; Shimizu, K.; Osawa, K. J. Periodontol. 2008, 79, 1378.
(b) Kashiwada, Y.; Nonaka, G. I.; Nishioka, I.; Chang, J. J.; Lee, K. H. J. Nat. Prod. 1992, 55, 1033.
[54] (a) De Boggiatto, M. V.; De Heluani, C. S.; De Fenik, I. J.; Catalan, C. A. J. Org. Chem. 1987, 52, 1505.
(b) Wei, G. L.; Rosazza, J. P. Tetrahedron Lett. 1990, 31, 2833.
(c) Peters, R.; Fischer, D. F. Angew. Chem., Int. Ed. 2006, 45, 5736.
[55] Xia, A.-B.; Pan, G.-J.; Wu, C.; Liu, X.-L.; Zhang, X.-L.; Li, Z.-B.; Du, X.-H.; Xu, D.-Q. Adv. Synth. Catal. 2016, 358, 3155.
[56] (a) Cabrera, S.; Aleman, J.; Bolze, P.; Bertelsen, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2008, 47, 121.
(b) Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498.
(c) Varga, S.; Jakab, G.; Drahos, L.; Holczbauer, T.; Czugler, M.; Soós, T. Org. Lett. 2011, 13, 5416.
[57] (a) Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416.
(b) Lathrop, S. P.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 13628.
(c) Scroggins, S. T.; Chi, Y.; Fréchet, J. M. Angew. Chem., Int. Ed. 2010, 49, 2393.
(d) Wang, C.; Han, Z. Y.; Luo, H. W.; Gong, L. Z. Org. Lett. 2010, 12, 2266.
[58] Enders, D.; Schmid, B.; Erdmann, N.; Raabe, G. Synthesis 2010, 2271.
[59] Mao, Z.; Jia, Y.; Xu, Z.; Wang, R. Adv. Synth. Catal. 2012, 354, 1401.
[60] Han, B.; Huang, W.; Ren, W.; He, G.; Wang, J. H.; Peng, C. Adv. Synth. Catal. 2015, 357, 561.
[61] Raja, A.; Hong, B. C.; Liao, J. H.; Lee, G. H. Org. Lett. 2016, 18, 1760.
[62] (a) S Hamama, W.; G El-Gohary, H.; Kuhnert, N.; H Zoorob, H. Curr. Org. Chem. 2012, 16, 373.
(b) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
(c) Brune, K. Acute Pain 1997, 1, 33.
[63] (a) Yoshida, H.; Yanai, H.; Namiki, Y.; Fukatsu-Sasaki, K.; Furutani, N.; Tada, N. CNS Drug Rev. 2006, 12, 9.
(b) Hadi, V.; Koh, Y. H.; Sanchez, T. W.; Barrios, D.; Neamati, N.; Jung, K. W. Bioorg. Med. Chem. Lett. 2010, 20, 6854.
(c) Chande, M. S.; Barve, P. A.; Suryanarayan, V. J. Heterocycl. Chem. 2007, 44, 49.
[64] Li, J. H.; Cui, Z. H.; Du, D. M. Org. Chem. Front. 2016, 3, 1087.
Options
Outlines

/

〈 〉