One-pot organocatalytic enantioselective Michael addition and aza-cyclization/dehydration cascade reaction strategy: Asymmetric synthesis of highly functionalized 1,4-dihydroquinolines

Tetrahedron Letters

Volumn 56, Issue 33, 2015, Pages 4819-4823

  Kim, Hanna ^a   Kim, Sung Gon ^a  

^a Kyonggi University   (South Korea)

Author keywords

1,4 Dihydroquinoline; Asymmetric catalysis; Cascade reaction; Michael reaction; Organocatalysis

Indexed keywords

2 AMINO BETA NITROSTYRENE; DIHYDROQUINOLINE DERIVATIVE; ESTER DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; AZA CYCLIZATION DEHYDRATION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CINCHONA; CYCLIZATION; ENANTIOSELECTIVITY; MICHAEL ADDITION; ONE POT SYNTHESIS;

EID: 84936985369     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.06.071     Document Type: Article

References (76)

1. D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem., Int. Ed. 46 2007 1570
2. X. Yu, and W. Wang Org. Biomol. Chem. 6 2008 2037
3. C. Grondal, M. Jeanty, and D. Enders Nat. Chem. 2 2010 167
4. Ł. Albrecht, H. Jiang, and K.A. Jørgensen Angew. Chem., Int. Ed. 50 2011 8492
5. H. Pellissier Adv. Synth. Catal. 354 2012 237
6. H. Pellissier Asymmetric Domino Reactions 2013 RSC Cambridge
7. C.M.R. Volla, I. Atodiresei, and M. Rueping Chem. Rev. 1114 2014 2390
8. A.R. Katritzky, S. Rachwal, and B. Rachwal Tetrahedron 52 1996 15031
9. V. Kouznetsov, A. Palma, C. Ewert, and A. Varlamov J. Heterocycl. Chem. 35 1998 761
10. A. Mitchinson, and A. Nadin J. Chem. Soc., Perkin Trans. 1 17 2000 2862
11. Y.-G. Zhou Acc. Chem. Res. 40 2007 1357
12. V. Sridharan, P.A. Suryavanshi, and J.C. Menéndez Chem. Rev. 111 2011 7157
13. C.Z. Ding, J.T. Hunt, C. Ricca, and V. Manne Bioorg. Med. Chem. Lett. 10 2000 273
14. J.M. Urbina, J.C.G. Cortés, A. Palma, S.N. López, S.A. Zacchino, R.D. Enriz, J.C. Ribas, and V.V. Kouznetzov Bioorg. Med. Chem. 8 2000 691
15. J.-P. Liou, Z.-Y. Wu, C.-C. Kuo, C.-Y. Chang, P.-Y. Lu, C.-M. Chen, H.-P. Hsieh, and J.-Y. Chang J. Med. Chem. 51 2008 4351
16. E. Ramesh, R.D.R.S. Manian, R. Raghunathan, S. Sainath, and M. Raghunathan Bioorg. Med. Chem. 17 2009 660
17. R.T. Skerlj, G.J. Bridger, A. Kaller, E.J. McEachern, J.B. Crawford, Y. Zhou, B. Atsma, J. Langille, S. Nan, D. Veale, T. Wilson, C. Hartwig, S. Hatse, K. Princen, E. De Clercq, and D. Schols J. Med. Chem. 53 2010 3376
18. M. Rueping, A.P. Antonchick, and T. Theissmann Angew. Chem., Int. Ed. 45 2006 3683
19. S. Fustero, J. Moscardó, D. Jiménez, M.D. Pérez-Carrión, M. Sánche-Roselló, and C. del Pozo Chem. Eur. J. 14 2008 9868
20. H. Xu, S.J. Zuend, M.G. Woll, Y. Tao, and E.N. Jacobsen Science 327 2010 986
21. M. Xie, X. Chen, Y. Zhu, B. Gao, L. Lin, X. Liu, and X. Feng Angew. Chem., Int. Ed. 49 2010 3799
22. Y.K. Kang, S.M. Kim, and D.Y. Kim J. Am. Chem. Soc. 132 2010 11847
23. Z.-X. Jia, Y.-C. Luo, and P.-F. Xu Org. Lett. 13 2011 832
24. G. Dickmeiss, K.L. Jensen, D. Worgull, P.T. Franke, and K.A. Jørgensen Angew. Chem., Int. Ed. 50 2011 1580
25. K. Mori, K. Ehara, K. Kurihara, and T. Akiyama J. Am. Chem. Soc. 133 2011 6166
26. G. Dagousset, J.-P. Zhu, and G. Masson J. Am. Chem. Soc. 133 2011 14804
27. L. Ren, T. Lei, J.-X. Ye, and L.-Z. Gong Angew. Chem., Int. Ed. 51 2012 771
28. H.R. Tan, H.F. Ng, J. Chang, and J. Wang Chem. Eur. J. 18 2012 3865
29. Z.-X. Jia, Y.-C. Luo, Y. Wang, L. Chen, P.-F. Xu, and B. Wang Chem. Eur. J. 18 2012 12958
30. W. Yang, H.-X. He, Y. Gao, and D.-M. Du Adv. Synth. Catal. 355 2013 3670
31. C. Luo, and Y. Huang J. Am. Chem. Soc. 135 2013 8193
32. S.W. Elmore, M.J. Coghlan, D.D. Anderson, J.K. Pratt, B.E. Green, A.X. Wang, M.A. Stashko, C.W. Lin, C.M. Tyree, J.N. Miner, P.B. Jacobson, D.M. Wilcox, and B.C. Lane J. Med. Chem. 44 2001 4481
33. L. Foucout, F. Gourand, M. Dhilly, P. Bohn, G. Dupas, J. Costentin, A. Abbas, F. Marsais, L. Barre, and V. Levacher Org. Biomol. Chem. 7 2009 3666
34. J. Fotie, M. Kaiser, D.A. Delfin, J. Manley, C.S. Reid, J.-M. Paris, T. Wenzler, L. Maes, K.V. Mahasenan, C. Li, and K.A. Werbovetz J. Med. Chem. 53 2010 966
35. P.A. Evans, J.E. Robinson, and K.K. Moffett Org. Lett. 3 2001 3269
36. S.J. Pastine, S.-W. Youn, and D. Sames Tetrahedron 59 2003 8859
37. P.D. Pohlhaus, R.K. Bowman, and J.S. Johnson J. Am. Chem. Soc. 126 2004 2294
38. L. Cointeaus, and A. Alexakia Tetrahedron: Asymmetry 16 2005 925
39. G.-L. Lu, and H.C. Malinakova J. Org. Chem. 69 2004 4701
40. H. Li, J. Wang, H. Xie, L. Zu, W. Jiang, E.N. Duesler, and W. Wang Org. Lett. 9 2007 965
41. X. Liu, and Y. Lu Org. Biomol. Chem. 8 2010 4063
42. J.D. Shields, D.T. Ahneman, T.J.A. Graham, and A.G. Doyle Org. Lett. 16 2014 142
43. F. Rezgui, P. Mangeney, and A. Alexakis Tetrahedron Lett. 40 1999 6241
44. X. Zhang, X. Song, H. Li, S. Zhang, X. Chen, X. Yu, and W. Wang Angew. Chem., Int. Ed. 51 2012 7282
45. Y. Lee, and S.-G. Kim J. Org. Chem. 79 2014 8234
46. J.P. Malerich, K. Hagihara, and V.H. Rawal J. Am. Chem. Soc. 130 2008 14416
47. Z.-H. Zhang, X.-Q. Dong, D. Chen, and C.-J. Wang Chem. Eur. J. 14 2008 8780
48. R. Manzano, J.M. Andrés, M.D. Muruzábal, and R. Pedrosa Adv. Synth. Catal. 352 2010 3364
49. K. Murai, S. Fukushima, A. Nakamura, M. Shimura, and H. Fujioka Tetrahedron 67 2011 4862
50. H.Y. Bae, S. Some, J.S. Oh, Y.S. Lee, and C.E. Song Chem. Commun. 2011 9621
51. P. Chauhan, S.S. Chimni, and J. Asian Org. Chem. 1 2012 138
52. P. Kasaplar, P. Riente, C. Hartmann, and M.A. Pericàs Adv. Synth. Catal. 354 2012 2905
53. A. Lattanzi, C.D. Fusco, A. Russo, A. Poater, and L. Cavallo Chem. Commun. 2012 1650
54. C.C.J. Loh, P. Chauhan, D. Hack, and C. Lehmann Adv. Synth. Catal. 356 2014 3181
55. E. Zhou, B. Liu, and C. Dong Tetrahedron: Asymmetry 25 2014 181
56. O.D. Engl, S.P. Fritz, A. Ka¨slin, and H. Wannemers Org. Lett. 16 2014 5454
57. K.S. Rao, R. Trivedi, and M.L. Kantam Synlett 2015 221
58. M. Işik, M.Y. Unver, and C. Tanyeli J. Org. Chem. 80 2015 828
59. T. Okino, Y. Hoashi, and Y. Takemoto J. Am. Chem. Soc. 125 2003 12672
60. S. Sakamoto, T. Inokuma, and Y. Takemoto Org. Lett. 13 2011 6374
61. T. Marcelli, J.H.V. Maarseveen, and H. Hiemstra Angew. Chem., Int. Ed. 45 2006 7496
62. S.J. Connon Chem. Commun. 2008 2499
63. C.E. Song Cinchona Alkaloids in Synthesis & Catalysis 2009 Wiley-VCH Weinheim
64. Y. Takemoto Chem. Pharm. Bull. 58 2010 593
65. B. Han, J.-L. Li, Y.-C. Xiao, S.-L. Zhou, and Y.-C. Chen Curr. Org. Chem. 15 2011 4128
66. E. Marques-Lopez, and R.P. Herrera B. Pignataro, New Strategies in Chemical Synthesis and Catalysis 2010 Wiley-VCH Weinheim 175
67. J. Alemán, A. Parra, H. Jiang, and K.A. Jørgensen Chem. Eur. J. 17 2011 6890
68. P. Chauhan, S. Mahajan, U. Kaya, D. Hack, and D. Enders Adv. Synth. Catal. 357 2015 253
69. r = 11.9 min.
70. In the case of successive aza-cyclization/dehydration reaction using boron trifluoride diethyl etherate in toluene without exchanging the solvent, the reaction was not proceeded to provide the 1,4-dihydroquinoline.
71. D. Enders, G. Urbanietz, and G. Raabe Synthesis 2011 1905
72. B. Tan, Y. Lu, X. Zeng, P.J. Chua, and G. Zhong Org. Lett. 12 2010 2682
73. O. Baslé, W. Raimondi, M.M.S. Duque, D. Bonne, T. Constantieux, and J. Rodriguez Org. Lett. 12 2010 5246
74. X.-F. Wang, Q.-L. Hua, Y. Cheng, X.-L. An, Q.Q. Yang, J.-R. Chen, and W.-J. Xiao Angew. Chem., Int. Ed. 49 2010 8379
75. J.L. Zhu, Y. Zhang, C. Liu, A.-M. Zheng, and W. Wang J. Org. Chem. 77 2012 9813
76. X. Li, C. Yang, J.-L. Jin, X.-S. Xue, and J.-P. Cheng Chem. Asian J. 8 2013 997