Organocatalytic synthesis of highly functionalized pyridines at room temperature

Angewandte Chemie - International Edition

Volumn 52, Issue 33, 2013, Pages 8584-8587

  Shi, Zugui ^b   Loh, Teck Peng ^a,b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b Nanyang Technological University   (Singapore)

Author keywords

amines; cyclization; heterocycles; organocatalysis; synthetic methods

Indexed keywords

CASCADE REACTIONS; FUNCTIONALIZED PYRIDINES; HETEROCYCLES; MILD REACTION CONDITIONS; ORGANOCATALYSIS; ORGANOCATALYTIC; ROOM TEMPERATURE; SYNTHETIC METHODS;

AMINES; CATALYSIS; PYRIDINE; REACTION KINETICS;

CYCLIZATION;

ALLENOLIC ACID; AMINE; NA(MU (T)BU)(MU TMP)ZN((T)BU); NA(MU-(T)BU)(MU-TMP)ZN((T)BU); NAPHTHALENE DERIVATIVE; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HETEROCYCLES; ORGANOCATALYSIS; SYNTHESIS; SYNTHETIC METHODS; TEMPERATURE;

AMINES; CYCLIZATION; HETEROCYCLES; ORGANOCATALYSIS; SYNTHETIC METHODS;

CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; PYRIDINES; SULFONIC ACIDS; TEMPERATURE;

EID: 84882326625     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201301519     Document Type: Article

References (91)

1. J. P. Michael, Nat. Prod. Rep. 2005, 22, 627
2. M. Abass, Heterocycles 2005, 65, 901
3. G. Jones, in Comprehensive Heterocyclic Chemistry, Vol. 5 (Eds.:, A. R. Katritzky, C. W. Rees, E. F. V. Scriven,), Pergamon, Oxford, 1996, p. 167
4. J. A. Joule, K. Mills In, heterocyclic Chemistry, 4 th ed. Wiley-Blackwell, Oxford, 2000
5. J. S. Carey, D. Laffan, C. homson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337
6. V. C. Gibson, C. Redshaw, G. A. Solan, Chem. Rev. 2007, 107, 1745.
7. J. A. Varela, C. Saa, Chem. Rev. 2003, 103, 3787
8. G. D. Henry, Tetrahedron 2004, 60, 6043
9. G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644
10. M. A. Ciufolini, B. K. Chan, Heterocycles 2007, 74, 101
11. B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085
12. M. C. Bagley, C. Glover, E. A. Merrit, Synlett 2007, 2459
13. B. Groenendaal, E. Ruijter, R. V. A. Orru, Chem. Commun. 2008, 5474
14. M. D. Hill, Chem. Eur. J. 2010, 16, 12052.
15. M. M. McCormick, H. A. Duong, G. Zuo, J. Louie, J. Am. Chem. Soc. 2005, 127, 5030
16. R. Tanaka, A. Yuza, Y. Watai, D. Suzuki, Y. Takayam, F. Sato, H. Urabe, J. Am. Chem. Soc. 2005, 127, 7774
17. M. Movassaghi, M. D. Hill, J. Am. Chem. Soc. 2006, 128, 4592
18. Y. Yamamoto, K. Kinpara, R. Ogawa, H. Nishiyama, K. Itoh, Chem. Eur. J. 2006, 12, 5618
19. J. Dash, T. Lechel, H.-U. Reissig, Org. Lett. 2007, 9, 5541
20. B. M. Trost, A. C. Gutierrez, Org. Lett. 2007, 9, 1473
21. J. Barluenga, M. A. Fernández-Rodríguez, P. García-García, E. Aguilar, J. Am. Chem. Soc. 2008, 130, 2764
22. J. R. Manning, H. M. L. Davies, J. Am. Chem. Soc. 2008, 130, 8602
23. S. Liu, L. S. Liebeskind, J. Am. Chem. Soc. 2008, 130, 6918
24. K. Parthasarathy, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2008, 10, 325
25. T. Sasada, N. Sakai, T. Konakahara, J. Org. Chem. 2008, 73, 6905
26. S. Chiba, Y.-J. Xu, Y.-F. Wang, J. Am. Chem. Soc. 2009, 131, 12886
27. Y. F. Wang, S. Chiba, J. Am. Chem. Soc. 2009, 131, 12570
28. I. Nakamura, D. Zhang, M. Terada, J. Am. Chem. Soc. 2010, 132, 7884
29. M. Ohashi, I. Takeda, M. Ikawa, S. Ogoshi, J. Am. Chem. Soc. 2011, 133, 18018
30. C. Wang, X. Li, F. Wu, B. Wan, Angew. Chem. 2011, 123, 7300
31. Angew. Chem. Int. Ed. 2011, 50, 7162
32. S. Yamamoto, K. Okamoto, M. Murakoso, Y. Kuninobu, K. Takai, Org. Lett. 2012, 14, 3182
33. W. Gati, M. M. Rammah, M. B. Rammah, F. Couty, G. Evano, J. Am. Chem. Soc. 2012, 134, 9078.
34. J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035
35. C. E. Aroyan, A. Dermenci, S. J. Miller, Tetrahedron 2009, 65, 4069. For selected examples of intramolecular Rauhut-Currier reaction, see
36. P. M. Brown, N. Káppel, P. J. Murphy, Tetrahedron Lett. 2002, 43, 8707
37. E. Marqués-López, R. P. Herrera, T. Marks, W. C. Jacobs, D. Köning, R. M. Figueiredo, M. Christmann, Org. Lett. 2009, 11, 4116
38. J. E. Wilson, J. Sun, G. C. Fu, Angew. Chem. 2010, 122, 165
39. Angew. Chem. Int. Ed. 2010, 49, 161
40. Y. Qiao, S. Kumar, W. P. Malachowski, Tetrahedron Lett. 2010, 51, 2636
41. X.-F. Wang, L. Peng, J. An, C. Li, Q.-Q. Yang, L.-Q. Lu, F.-L. Gu, W.-J. Xiao, Chem. Eur. J. 2011, 17, 6484
42. J.-J. Gong, T.-Z. Li, K. Pan, X.-Y. Wu, Chem. Commun. 2011, 47, 1491
43. S. Takizawa, T. M. Nguyen, A. Grossmann, D. Enders, H. Sasai, Angew. Chem. 2012, 124, 5519
44. Angew. Chem. Int. Ed. 2012, 51, 5423
45. P. S. Selig, S. J. Miller, Tetrahedron Lett. 2011, 52, 2148.
46. T. E. Reynolds, M. S. Binkley, K. A. Scheidt, Org. Lett. 2008, 10, 2449
47. C. Zhong, Y. Chen, J. L. Petersen, N. G. Akhmedov, X. Shi, Angew. Chem. 2009, 121, 1305
48. Angew. Chem. Int. Ed. 2009, 48, 1279
49. P. Shanbhag, P. R. Nareddy, M. Dadwal, S. M. Mobin, I. N. N. Namboothiri, Org. Biomol. Chem. 2010, 8, 4867
50. Q.-Y. Zhao, C.-K. Pei, X.-Y. Guan, M. Shi, Adv. Synth. Catal. 2011, 353, 1973
51. Z. Shi, Q. Tong, W. W. Y. Leong, G. Zhong, Chem. Eur. J. 2012, 18, 9802
52. Z. Shi, P. Yu, T.-P. Loh, G. Zhong, Angew. Chem. 2012, 124, 7945
53. Angew. Chem. Int. Ed. 2012, 51, 7825.
54. C. E. Aroyan, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 256
55. C. E. Aroyan, A. Dermenci, S. J. Miller, J. Org. Chem. 2010, 75, 5784.
56. S. France, D. J. Guerin, S. J. Miller, T. Lectka, Chem. Rev. 2003, 103, 2985
57. G. C. Fu, Acc. Chem. Res. 2004, 37, 542
58. R. P. Wurz, Chem. Rev. 2007, 107, 5570
59. S. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621
60. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248
61. Angew. Chem. Int. Ed. 2004, 43, 5138
62. B. List, Acc. Chem. Res. 2004, 37, 548
63. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580
64. M. J. Gaunt, C. C. C. Johansson, Chem. Rev. 2007, 107, 5596
65. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590
66. Angew. Chem. Int. Ed. 2007, 46, 1570
67. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232
68. Angew. Chem. Int. Ed. 2008, 47, 6138
69. D. W. C. MacMillan, Nature 2008, 455, 304
70. S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584
71. Angew. Chem. Int. Ed. 2008, 47, 1560. For selected amine catalyzed reactions, see
72. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243
73. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395
74. G. Zhong, Angew. Chem. 2003, 115, 4379
75. Angew. Chem. Int. Ed. 2003, 42, 4247
76. J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjrsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296
77. Z. Tang, Z.-H. Yang, X.-H. Chen, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, J. Am. Chem. Soc. 2005, 127, 9285
78. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284
79. Angew. Chem. Int. Ed. 2005, 44, 4212
80. J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393
81. Angew. Chem. Int. Ed. 2007, 46, 389
82. Z. Shi, P. Yu, P. J. Chua, G. Zhong, Adv. Synth. Catal. 2009, 351, 2797
83. Z. Shi, B. Tan, W. W. Y. Leong, X. Zeng, M. Lu, G. Zhong, Org. Lett. 2010, 12, 5402
84. J. Xiao, F.-X. Xu, Y.-P. Lu, T.-P. Loh, Org. Lett. 2010, 12, 1220.
85. C. A. Evans, S. J. Miller, J. Am. Chem. Soc. 2003, 125, 12394
86. W. Yao, Y. Wu, G. Wang, Y. Zhang, C. Ma, Angew. Chem. 2009, 121, 9893
87. Angew. Chem. Int. Ed. 2009, 48, 9713
88. H. Liu, Q. Zhang, L. Wang, X. Tong, Chem. Commun. 2010, 46, 312
89. W. Liu, J. Zhou, C. Zheng, X. Chen, H. Xiao, Y. Yang, Y. Guo, G. Zhao, Tetrahedron 2011, 67, 1768
90. X. Wang, T. Fang, X. Tong, Angew. Chem. 2011, 123, 5473
91. Angew. Chem. Int. Ed. 2011, 50, 5361.