Ruthenium(II)/chiral Brønsted acid co-catalyzed enantioselective four-component reaction/cascade aza-michael addition for efficient construction of 1,3,4-tetrasubstituted tetrahydroisoquinolines

Chemistry - A European Journal

Volumn 20, Issue 6, 2014, Pages 1505-1509

  Jiang, Jun ^a   Ma, Xiaochu ^a   Ji, Changge ^a   Guo, Zhenqiu ^a   Shi, Taoda ^a   Liu, Shunying ^a   Hu, Wenhao ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Br nsted acid; multicomponent reactions; ruthenium; synergistic catalysis; tetrahydroisoquinolines

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; ENANTIOMERS; ENANTIOSELECTIVITY; RUTHENIUM;

AZA-MICHAEL ADDITION; AZA-MICHAEL REACTION; DIASTEREO- AND ENANTIOSELECTIVITY; EFFICIENT CONSTRUCTION; MULTI-COMPONENT REACTIONS; SYNERGISTIC CATALYSIS; TETRAHYDROISOQUINOLINES; TETRAHYDROQUINOLINES;

RUTHENIUM COMPOUNDS;

COORDINATION COMPOUND; RUTHENIUM; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; BRØNSTED ACID; CATALYSIS; CHEMISTRY; MULTICOMPONENT REACTIONS; STEREOISOMERISM; SYNERGISTIC CATALYSIS; SYNTHESIS;

BRØNSTED ACID; MULTICOMPONENT REACTIONS; RUTHENIUM; SYNERGISTIC CATALYSIS; TETRAHYDROISOQUINOLINES;

CATALYSIS; COORDINATION COMPLEXES; RUTHENIUM; STEREOISOMERISM; TETRAHYDROISOQUINOLINES;

EID: 84895063522     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201304576     Document Type: Article

References (68)

1. D. Enders, C. Grondal, M. R. M. Huttl, Angew. Chem. 2007, 119, 1590
2. Angew. Chem. Int. Ed. 2007, 46, 1570
3. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167-178
4. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
5. Angew. Chem. Int. Ed. 2006, 45, 7134
6. L. F. Tietze, Chem. Rev. 1996, 96, 115.
7. A. Fayol, J. P. Zhu, Angew. Chem. 2002, 114, 3785
8. Angew. Chem. Int. Ed. 2002, 41, 3633
9. Y. G. Chi, S. T. Scroggins, J. M. J. Frechet, J. Am. Chem. Soc. 2008, 130, 6322
10. W. Shu, G. C. Jia, S. M. Ma, Angew. Chem. 2009, 121, 2826
11. Angew. Chem. Int. Ed. 2009, 48, 2788
12. J. Jiang, X. Y. Guan, S. Y. Liu, B. Y. Ren, X. C. Ma, X. Guo, F. P. Lv, X. Wu, W. H. Hu, Angew. Chem. 2013, 125, 1579
13. Angew. Chem. Int. Ed. 2013, 52, 1539.
14. G. Maas, Chem. Soc. Rev. 2004, 33, 183
15. B. M. Toste, F. D. Toste, A. B. Pinkerton, Chem. Rev. 2001, 101, 2067.
16. M. Zhang, X. J. Fang, H. Neumann, M. Beller, J. Am. Chem. Soc. 2013, 135, 11384
17. K. Inamoto, J. Kadokawa, Y. Kondo, Org. Lett. 2013, 15, 3962.
18. D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77-80.
19. Q. Cai, Z. A. Zhao, S. L. You, Angew. Chem. 2009, 121, 7564
20. Angew. Chem. Int. Ed. 2009, 48, 7428
21. Q. Cai, X. W. Liang, S. G. Wang, J. W. Zhang, X. Zhang, S. L. You, Org. Lett. 2012, 14, 5022.
22. E. Galardon, P. L. Maux, G. Simonneaux, J. Chem. Soc. Perkin Trans. 1 1997, 2455
23. E. Galardon, P. L. Maux, G. Simonneaux, Tetrahedron 2000, 56, 615.
24. A. Del Zotto, W. Baratta, P. Rigo, J. Chem. Soc. Perkin Trans. 1 1999, 3079.
25. Q. H. Deng, H. W. Xu, A. W. H. Yuen, Z. J. Xu, C. M. Che, Org. Lett. 2008, 10, 1529.
26. Y. H. Wang, Y. X. Zhu, Z. Y. Chen, A. Q. Mi, W. H. Hu, M. P. Doyle, Org. Lett. 2003, 5, 3923
27. Y. H. Wang, Z. Y. Chen, A. Q. Mi, W. H. Hu, Chem. Commun. 2004, 2486
28. H. X. Huang, Y. H. Wang, Z. Y. Chen, W. H. Hu, Adv. Synth. Catal. 2005, 347, 531
29. Y. G. Zhu, C. W. Zhai, Y. L. Yue, L. P. Yang, W. H. Hu, Chem. Commun. 2009, 1362
30. J. Jiang, H. D. Xu, J. B. Xi, B. Y. Ren, F. P. Lv, X. Guo, L. Q. Jiang, Z. Y. Zhang, W. H. Hu, J. Am. Chem. Soc. 2011, 133, 8428
31. J. Jiang, X. C. Ma, S. Y. Liu, Y. Qian, F. P. Lv, L. Q, X. Wu, W. H. Hu, Chem. Commun. 2013, 49, 4238.
32. D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804
33. D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2005, 127, 9360
34. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592
35. Angew. Chem. Int. Ed. 2004, 43, 1566
36. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999
37. T. Akiyama, Chem. Rev. 2007, 107, 5744.
38. X. F. Xu, J. Zhou, L. P. Yang, W. H. Hu, Chem. Commun. 2008, 6564.
39. For a comprehensive account of the chemistry and biology of these compounds, see:, J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669
40. for a review, see:, T. Ozturk, The Alkaloids, Vol. 53 (Ed.:, G. A. Cordell,), Academic Press, San Diego, 2000, p. 120.
41. S. J. Danishefsky, P. J. Harrison, R. R. Webb II, B. T. O'Neill, J. Am. Chem. Soc. 1985, 107, 1421
42. H. Saito, T. Hirata, Tetrahedron Lett. 1987, 28, 4065
43. S. Saito, O. Tamura, Y. Kobayashi, F. Matsuda, T. Katoh, S. Terashima, Tetrahedron 1994, 50, 6193
44. S. Saito, K. Tanaka, K. Nakatani, F. Matsuda, T. Katoh, S. Terashima, Tetrahedron 1994, 50, 6209
45. T. Katoh, Y. Nagata, Y. Kobayashi, K. Arai, J. Minami, S. Terashima, Tetrahedron 1994, 50, 6221
46. T. Katoh, M. Kirihara, T. Yoshino, O. Tamura, F. Ikeuchi, K. Nakatani, F. Matsuda, K. Yamada, K. Gomi, T. Ashizawa, S. Terashima, Tetrahedron 1994, 50, 6259
47. M. E. Flanagan, R. M. Williams, J. Org. Chem. 1995, 60, 6791
48. M. C. McMills, D. L. Wright, J. D. Zubkowski, E. J. Valente, Tetrahedron Lett. 1996, 37, 7205
49. O. Koepler, S. Laschat, A. Baro, P. Fischer, B. Miehlich, M. Hotfilder, C. le Viseur, Eur. J. Org. Chem. 2004, 3611
50. U. Schneider, X. Pannecoucke, J. C. Quirion, Synlett 2005, 1853.
51. G. J. Aune, T. Furuta, Y. Pommier, Anti-Cancer Drugs 2002, 13, 545.
52. J. M. Frincke, D. J. Faulkner, J. Am. Chem. Soc. 1982, 104, 265
53. H. He, D. J. Faulkner, J. Org. Chem. 1989, 54, 5822
54. B. S. Davidson, Tetrahedron Lett. 1992, 33, 3721
55. P. S. Parameswaran, C. G. Naik, S. Y. Kamat, B. N. Pramanik, Indian J. Chem. Sect. B 1998, 37, 1258
56. A. Fontana, P. Cavaliere, S. Wahidulla, C. G. Naik, G. Cimino, Tetrahedron 2000, 56, 7305.
57. A. Iimuro, K. Yamaji, S. Kandula, T. Nagano, Y. Kita, K. Mashima, Angew. Chem. 2013, 125, 2100
58. Angew. Chem. Int. Ed. 2013, 52, 2046
59. Z. S. Ye, R. N. Guo, X. F. Cai, M. W. Chen, L. Shi, Y. G. Zhou, Angew. Chem. 2013, 125, 3773
60. Angew. Chem. Int. Ed. 2013, 52, 3685
61. J. H. Xie, P. C. Yan, Q. Q. Zhang, K. X. Yuan, Q. L. Zhou, ACS Catal. 2012, 2, 561
62. F. Berhal, Z. Wu, Z. G. Zhang, T. Ayad, V. R. Vidal, Org.Lett. 2012, 14, 3308.
63. C. Bolchi, M. Pallavicini, L. Fumagalli, V. Straniero, E. Valoti, Org. Process Res. Dev. 2013, 17, 432.
64. P. Magnus, K. S. Matthews, J. Am. Chem. Soc. 2005, 127, 12476
65. M. X. Chang, W. Li, X. M. Zhang, Angew. Chem. 2011, 123, 10867
66. Angew. Chem. Int. Ed. 2011, 50, 10679
67. M. Rueping, T. Theissmann, M. Stoeckel, A. P. Antonchick, Org. Biomol. Chem. 2011, 9, 6844.
68. Gaussian 09 (Revision B01), M. J. Frisch, et al., Gaussian, Inc., Wallingford CT, 2010.