Asymmetric synthesis of tetrahydroquinolines with quaternary stereocenters through the Povarov reaction

Chemistry - A European Journal

Volumn 17, Issue 49, 2011, Pages 13800-13805

  Xie, Mingsheng ^a   Liu, Xiaohua ^a   Zhu, Yin ^a   Zhao, Xiaohu ^a   Xia, Yong ^a   Lin, Lili ^a   Feng, Xiaoming ^a  

^a Sichuan University   (China)

Author keywords

asymmetric catalysis; dioxides; Povarov reaction; scandium; tetrahydroquinolines

Indexed keywords

ALDIMINES; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; DIASTEREO-SELECTIVITY; DIENOPHILES; DIOXIDES; ENANTIOPURE; GRAM SCALE; POVAROV REACTION; QUATERNARY STEREOCENTERS; QUINOLINE DERIVATIVE; SIDE REACTIONS; TETRAHYDROQUINOLINE; TETRAHYDROQUINOLINES;

CATALYSIS; ENANTIOSELECTIVITY; HYDROGEN; SCANDIUM; STYRENE;

SYNTHESIS (CHEMICAL);

EID: 82455219457     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102333     Document Type: Article

References (85)

1. K. Fuji, Chem. Rev. 1993, 93, 2037-2066
2. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415
3. Angew. Chem. Int. Ed. 1998, 37, 388-401
4. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732
5. Angew. Chem. Int. Ed. 2001, 40, 4591-4597
6. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363-5367
7. D. J. Ramõn, M. Yus, Curr. Org. Chem. 2004, 8, 149-183
8. J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473-1482
9. B. M. Trost, C. H. Jiang, Synthesis 2006, 369-396
10. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969-5994
11. O. Riant, J. Hannedouche, Org. Biomol. Chem. 2007, 5, 873-888
12. M. Bella, T. Gasperi, Synthesis 2009, 1583-1614.
13. H.-H. Hennies, C. Maul, M. Przewosny, B. Sundermann, DE 10236910, 2004
14. R. Uchida, R. Imasato, K. Shiomi, H. Tomoda, S. Omura, Org. Lett. 2005, 7, 5701-5704
15. R. Uchida, R. Imasato, Y. Yamaguchi, R. Masuma, K. Shiomi, H. Tomoda, S. Omura, J. Antibiot. 2006, 59, 646-651
16. W. F. J. Karstens, P. G. M. Conti, C. M. Timmers, R. Plate, C. J. Van Koppen, WO 2009027482, 2009.
17. L. S. Povarov, Russ. Chem. Rev. 1967, 36, 656-670.
18. For a recent review of normal-electron-demand aza Diels-Alder reactions, see:, K. A. Jørgensen, Angew. Chem. 2000, 112, 3702-3733
19. Angew. Chem. Int. Ed. 2000, 39, 3558-3588.
20. S. Kobayashi, S. Komiyama, H. Ishitani, Angew. Chem. 1998, 110, 1026-1028
21. Angew. Chem. Int. Ed. 1998, 37, 979-981
22. S. Yao, M. Johannsen, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 1998, 110, 3318-3321
23. Angew. Chem. Int. Ed. 1998, 37, 3121-3124
24. S. Yao, S. Saaby, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J. 2000, 6, 2435-2448
25. N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018-4019
26. O. G. Mancheño, R. G. Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2004, 126, 456-457
27. H. Sundén, I. Ibrahem, L. Eriksson, A. Cõrdova, Angew. Chem. 2005, 117, 4955-4958
28. Angew. Chem. Int. Ed. 2005, 44, 4877-4880
29. J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914-4916
30. Angew. Chem. Int. Ed. 2006, 45, 4796-4798
31. D. J. Shang, J. G. Xin, Y. L. Liu, X. Zhou, X. H. Liu, X. M. Feng, J. Org. Chem. 2008, 73, 630-637
32. H. Mandai, K. Mandai, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 17961-17969.
33. A. R. Katritzky, S. Rachwal, B. Rachwal, Tetrahedron 1996, 52, 15031-15070
34. P. Buonora, J.-C. Olsen, T. Oh, Tetrahedron 2001, 57, 6099-6138
35. V. V. Kouznetsov, Tetrahedron 2009, 65, 2721-2750.
36. P. A. Grieco, A. Bahsas, Tetrahedron Lett. 1988, 29, 5855-5858
37. S. Kobayashi, H. Ishitani, S. Nagayama, Synthesis 1995, 1195-1202
38. S. Kobayashi, H. Ishitani, S. Nagayama, Chem. Lett. 1995, 423-424
39. J. S. Yadav, B. V. Subba Reddy, R. Srinivas, C. Madhuri, T. Ramalingam, Synlett 2001, 0240-0242
40. A. A. Kudale, J. Kendall, D. O. Miller, J. L. Collins, G. J. Bodwell, J. Org. Chem. 2008, 73, 8437-8447.
41. H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357-7360.
42. G. Sundararajan, N. Prabagaran, B. Varghese, Org. Lett. 2001, 3, 1973-1976
43. T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070-13071
44. H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. P. Zhu, J. Am. Chem. Soc. 2009, 131, 4598-4599
45. G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi, A. Ricci, Chem. Commun. 2010, 46, 327-329
46. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao, E. N. Jacobsen, Science 2010, 327, 986-990
47. M. S. Xie, X. H. Chen, Y. Zhu, B. Gao, L. L. Lin, X. H. Liu, X. M. Feng, Angew. Chem. 2010, 122, 3887-3890
48. Angew. Chem. Int. Ed. 2010, 49, 3799-3802
49. L. Bernardi, M. Comes-Franchini, M. Fochi, V. Leo, A. Mazzanti, A. Ricci, Adv. Synth. Catal. 2010, 352, 3399-3406
50. G. Dickmeiss, K. L. Jensen, D. Worgull, P. T. Franke, K. A. Jørgensen, Angew. Chem. 2011, 123, 1618-1621
51. Angew. Chem. Int. Ed. 2011, 50, 1580-1583.
52. T. Kametani, H. Takeda, Y. Suzuki, T. Honda, Heterocycles 1984, 22, 275-276
53. J. M. Mellor, G. D. Merriman, Tetrahedron 1995, 51, 6115-6132
54. S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1996, 118, 8977-8978
55. F. Linkert, S. Laschat, S. Kotila, T. Fox, Tetrahedron 1996, 52, 955-970
56. W. Zhang, X. D. Jia, L. Yang, Z.-L. Liu, Tetrahedron Lett. 2002, 43, 9433-9436
57. X. D. Jia, H. C. Lin, C. D. Huo, W. Zhang, J. M. Lü, L. Yang, G. Y. Zhao, Z.-L. Liu, Synlett 2003, 1707-1709.
58. H. Miyamura, K. Maehata, S. Kobayashi, Chem. Commun. 2010, 46, 8052-8054.
59. B. Crousse, J.-P. Bégué, D. Bonnet-Delpon, J. Org. Chem. 2000, 65, 5009-5013
60. V. V. Kouznetsov, C. Ochoa Puentes, A. R. Romero Bohõrquez, S. A. Zacchino, M. Sortino, M. Gupta, Y. Vázquez, A. Bahsas, J. Amaro-Luis, Lett. Org. Chem. 2006, 3, 300-304
61. V. V. Kouznetsov, C. M. Meléndez Gõmez, J. H. Bermúdez Jaimes, J. Heterocycl. Chem. 2010, 47, 1148-1152.
62. X. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res., 2011, 44, 547-587; for recent examples, see
63. Z. P. Yu, X. H. Liu, Z. H. Dong, M. S. Xie, X. M. Feng, Angew. Chem. 2008, 120, 1328-1331
64. Angew. Chem. Int. Ed. 2008, 47, 1308-1311
65. K. Zheng, J. Shi, X. H. Liu, X. M. Feng, J. Am. Chem. Soc. 2008, 130, 15770-15771
66. M. Kokubo, C. Ogawa, S. Kobayashi, Angew. Chem. 2008, 120, 7015-7017
67. Angew. Chem. Int. Ed. 2008, 47, 6909-6911
68. Y. L. Liu, D. J. Shang, X. Zhou, X. H. Liu, X. M. Feng, Chem. Eur. J. 2009, 15, 2055-2058
69. Y. Zhu, X. H. Chen, M. S. Xie, S. X. Dong, Z. Qiao, L. L. Lin, X. H. Liu, X. M. Feng, Chem. Eur. J. 2010, 16, 11963-11968
70. Y. F. Cai, X. H. Liu, Y. H. Hui, J. Jiang, W. T. Wang, W. L. Chen, L. L. Lin, X. M. Feng, Angew. Chem. 2010, 122, 6296-6300
71. Angew. Chem. Int. Ed. 2010, 49, 6160-6164
72. W. Li, J. Wang, X. L. Hu, K. Shen, W. T. Wang, Y. Y. Chu, L. L. Lin, X. H. Liu, X. M. Feng, J. Am. Chem. Soc. 2010, 132, 8532-8533
73. Y. Zhu, M. S. Xie, S. X. Dong, X. H. Zhao, L. L. Lin, X. H. Liu, X. M. Feng, Chem. Eur. J. 2011, 17, 8202-8208
74. W. D. Cao, X. H. Liu, W. T. Wang, L. L. Lin, X. M. Feng, Org. Lett. 2011, 13, 600-603
75. K. Zheng, C. K. Yin, X. H. Liu, L. L. Lin, X. M. Feng, Angew. Chem. 2011, 123, 2621-2625
76. Angew. Chem. Int. Ed. 2011, 50, 2573-2577
77. K. Shen, X. H. Liu, G. Wang, L. L. Lin, X. M. Feng, Angew. Chem. 2011, 123, 4780-4784
78. Angew. Chem. Int. Ed. 2011, 50, 4684-4688
79. Z. Wang, Z. G. Yang, D. H. Chen, X. H. Liu, L. L. Lin, X. M. Feng, Angew. Chem. 2011, 123, 5030-5034
80. Angew. Chem. Int. Ed. 2011, 50, 4928-4932
81. Y. F. Cai, X. H. Liu, J. Jiang, W. L. Chen, L. L. Lin, X. M. Feng, J. Am. Chem. Soc. 2011, 133, 5636-5639.
82. For a recent review on chiral scandium complexes in catalytic asymmetric reactions, see:, X. M. Feng, X. H. Liu, in Scandium: Compounds, Productions and Applications (Ed.:, V. A. Greene,), Nova Science, New York, 2011, pp. 1-48.
83. R. Leardini, D. Nanni, A. Tundo, G. Zanardi, F. Ruggieri, J. Org. Chem. 1992, 57, 1842-1848
84. N. Shindoh, H. Tokuyama, K. Takasu, Tetrahedron Lett. 2007, 48, 4749-4753
85. N. Shindoh, H. Tokuyama, Y. Takemoto, K. Takasu, J. Org. Chem. 2008, 73, 7451-7456.