Chiral Brønsted acid-catalyzed conjugate addition of indoles to azadienes: Enantioselective synthesis of hetero-triarylmethanes

doi:10.1016/S1872-2067(19)63396-6

Abstract

Abstract: An efficient chiral Brønsted acid-catalyzed conjugate addition of indoles to azadienes has been successfully developed, which enables a facile approach to optically active hetero-triarylmethanes with excellent enantioselectivities and broad substrate scope. This chiral Brønsted acid catalytic system provides a new opportunity for the development of asymmetric reactions of azadienes.

Key words: Conjugate addition, Hetero-triarylmethane, Azadiene, Indole, Chiral Brønsted acid

Huan-Ping Xie, Bo Wu, Xin-Wei Wang, Yong-Gui Zhou. Chiral Brønsted acid-catalyzed conjugate addition of indoles to azadienes: Enantioselective synthesis of hetero-triarylmethanes[J]. Chinese Journal of Catalysis, 2019, 40(10): 1566-1575.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(19)63396-6

https://www.cjcatal.com/EN/Y2019/V40/I10/1566

References

[1] T. P. Pathak, M. S. Sigman, J. Org. Chem., 2011, 76, 9210-9215.
[2] W.-J. Bai, J. G. David, Z.-G. Feng, M. G. Weaver, K.-L. Wu, T. R. R. Pettus, Acc. Chem. Res., 2014, 47, 3655-3664.
[3] M. S. Singh, A. Nagaraju, N. Anand, S. Chowdhury, RSC Adv., 2014, 4, 55924-55959.
[4] Z. Wang, J. Sun, Synthesis, 2015, 47, 3629-3644.
[5] L. Caruana, M. Fochi, L. Bernardi, Molecules, 2015, 20, 11733-11764.
[6] A. A. Jaworski, K. A. Scheidt, J. Org. Chem., 2016, 81, 10145-10153.
[7] B. Yang, S. Gao, Chem. Soc. Rev., 2018, 47, 7926-7953.
[8] J. Chen, Y. Huang, Org. Lett., 2017, 19, 5609-5612.
[9] J. Chen, P. Jia, Y. Huang, Org. Lett., 2018, 20, 6715-6718.
[10] L.-C. Yang, Z.-Q. Rong, Y.-N. Wang, Z. Y. Tan, M. Wang, Y. Zhao, Angew. Chem. Int. Ed., 2017, 56, 2927-2931.
[11] Z.-Q. Rong, L.-C. Yang, S. Liu, Z. Yu, Y.-N. Wang, Z. Y. Tan, R.-Z. Huang, Y. Lan, Y. Zhao, J. Am. Chem. Soc., 2017, 139, 15304-15307.
[12] Y.-N. Wang, L.-C. Yang, Z.-Q. Rong, T.-L. Liu, R. Liu, Y. Zhao, Angew. Chem. Int. Ed., 2018, 57, 1596-1600.
[13] Z.-Q. Rong, M. Wang, C. H. E. Chow, Y. Zhao, Chem.-Eur. J., 2016, 22, 9483-9487.
[14] K.-Q. Chen, Z.-H. Gao, S. Ye, Org. Chem. Front., 2019, 6, 405-409.
[15] Z.-H. Gao, K.-Q. Chen, Y. Zhang, L.-M. Kong, Y. Li, S. Ye, J. Org. Chem., 2018, 83, 15225-15235.
[16] H. Ni, X. Tang, W. Zheng, W. Yao, N. Ullah, Y. Lu, Angew. Chem. Int. Ed., 2017, 56, 14222-14226.
[17] Z. Gu, J. Zhou, G.-F. Jiang, Y.-G. Zhou, Org. Chem. Front., 2018, 5, 1148-1151.
[18] Z. Gu, J.-J. Xie, G.-F. Jiang, Y.-G. Zhou, Asian J. Org. Chem., 2018, 7, 1561-1564.
[19] W. Lin, C. Zhang, W. Xu, Y. Cheng, P. Li, W. Li, Adv. Synth. Catal., 2019, 361, 476-480.
[20] Z. Gu, B. Wu, G.-F. Jiang, Y.-G. Zhou, Chin. J. Chem., 2018, 36, 1130-1134.
[21] T. Akiyama, Chem. Rev., 2007, 107, 5744-5758.
[22] S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev., 2009, 38, 2190-2201.
[23] M. Zeng, S.-L. You, Synlett, 2010, 1289-1301.
[24] D. Kampen, C. M. Reisinger, B. List, Top. Curr. Chem., 2010, 291, 395-456.
[25] M. Terada, Synthesis, 2010, 1929-1982.
[26] A. Zamfir, S. Schenker, M. Freund, S. B. Tsogoeva, Org. Biomol. Chem., 2010, 8, 5262-5276.
[27] M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev., 2011, 40, 4539-4549.
[28] S. Schenker, A. Zamfir, M. Freund, S. B. Tsogoeva, Eur. J. Org. Chem., 2011, 2209-2222.
[29] M. Terada, Curr. Org. Chem., 2011, 15, 2227-2256.
[30] R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem., 2012, 4, 603-614.
[31] M. Mahlau, B. List, Angew. Chem. Int. Ed., 2013, 52, 518-533.
[32] D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev., 2014, 114, 9047-9153.
[33] F.-L. Sun, M. Zeng, Q. Gu, S.-L. You, Chem.-Eur. J., 2009, 15, 8709-8712.
[34] F.-L. Sun, X.-J. Zheng, Q. Gu, Q.-L. He, S.-L. You, Eur. J. Org. Chem., 2010, 47-50.
[35] M.-H. Zhuo, Y.-J. Jiang, Y.-S. Fan, Y. Gao, S. Liu, S. Zhang, Org. Lett., 2014, 16, 1096-1099.
[36] S. Qi, C.-Y. Liu, J.-Y. Ding, F.-S. Han, Chem. Commun., 2014, 50, 8605-8608.
[37] Y.-X. Gong, Q. Wu, H.-H. Zhang, Q.-N. Zhu, F. Shi, Org. Biomol. Chem., 2015, 13, 7993-8000.
[38] S. Saha, S. K. Alamsetti, C. Schneider, Chem. Commun., 2015, 51, 1461-1464.
[39] W. Zhao, Z. Wang, B. Chu, J. Sun, Angew. Chem. Int. Ed., 2015, 54, 1910-1913.
[40] Z. Wang, Y. F. Wong, J. Sun, Angew. Chem. Int. Ed., 2015, 54, 13711-13714.
[41] H.-H. Liao, A. Chatupheeraphat, C.-C. Hsiao, I. Atodiresei, M. Rueping, Angew. Chem. Int. Ed., 2015, 54, 15540-15544.
[42] J. Zheng, L. Lin, L. Dai, X. Yuan, X. Liu, X. Feng, Chem.-Eur. J., 2016, 22, 18254-18258.
[43] M.-H. Zhuo, G.-F. Liu, S.-L. Song, D. An, J. Gao, L. Zheng, S. Zhang, Adv. Synth. Catal., 2016, 358, 808-815.
[44] Y. Zhang, S.-X. Zhang, L.-N. Fu, Q.-X. Guo, ChemCatChem, 2017, 9, 3107-3110.
[45] C. Yue, F. Na, X. Fang, Y. Cao, J. C. Antilla, Angew. Chem. Int. Ed., 2018, 57, 11004-11008.
[46] P. Finocchiaro, D. Gust, K. Mislow, J. Am. Chem. Soc., 1974, 96, 3198-3205.
[47] H. V. Bossche, G. Willemsens, I. Roels, D. Bellens, H. Moereels, M. C. Coene, L. L. Jeune, W. Lauwers, P. A. J. Janssen, Biochem. Pharmacol., 1990, 40, 1707-1718.
[48] H. W. Gibson, S. H. Lee, P. T. Engen, P. Lecavalier, J. Sze, Y. X. Shen, M. Bheda, J. Org. Chem., 1993, 58, 3748-3756.
[49] G. Panda, Shagufta, J. K. Mishra, V. Chaturvedi, A. K. Srivastava, R. Srivastava, B. S. Srivastava, Bioorg. Med. Chem., 2004, 12, 5269-5276.
[50] R. S. Dothager, K. S. Putt, B. J. Allen, B. J. Leslie, V. Nesterenko, P. J. Hergenrother, J. Am. Chem. Soc., 2005, 127, 8686-8696.
[51] V. Nair, S. Thomas, S. C. Mathew, K. G. Abhilash, Tetrahedron, 2006, 62, 6731-6747.
[52] S. Gemma, G. Campiani, S. Butini, G. Kukreja, B. P. Joshi, M. Persico, B. Catalanotti, E. Novellino, E. Fattorusso, V. Nacci, L. Savini, D. Taramelli, N. Basilico, G. Morace, V. Yardley, C. Fattorusso, J. Med. Chem., 2007, 50, 595-598.
[53] S. D. Cho, K. Yoon, S. Chintharlapalli, M. Abdelrahim, P. Lei, S. Hamilton, S. Khan, S. K. Ramaiah, S. Safe, Cancer Res., 2007, 67, 674-683.
[54] R. Palchaudhuri, V. Nesterenko, P. J. Hergenrother, J. Am. Chem. Soc., 2008, 130, 10274-10281.
[55] M. K. Parai, G. Panda, V. Chaturvedi, Y. K. Manju, S. Sinha, Bioorg. Med. Chem. Lett., 2008, 18, 289-292.
[56] S. A. Snyder, S. P. Breazzano, A. G. Ross, Y. Lin, A. L. Zografos, J. Am. Chem. Soc., 2009, 131, 1753-1765.
[57] M. Shiri, M. A. Zolfigol, H. G. Kruger, Z. Tanbakouchian, Chem. Rev., 2010, 110, 2250-2293.
[58] X. Li, S. O. Lee, S. Stephen, Biochem. Pharmacol., 2012, 83, 1445-1455.
[59] CCDC number is 1878318. These details can be obtained free of charge via www.ccdc.com.ac.uk/data_request/ciffrom the Cambridge Crystallographic Data Centre.