Copper-catalyzed aerobic [3+2]-annulation of N -alkenyl amidines

Journal of the American Chemical Society

Volumn 134, Issue 8, 2012, Pages 3679-3682

  Wang, Yi Feng ^a   Zhu, Xu ^a   Chiba, Shunsuke ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ALUMINUM HYDRIDES; ANNULATION REACTIONS;

CATALYSIS;

COPPER;

ALKENE; ALUMINUM HYDRIDE; AMIDINE; COPPER; DIAMINE; N ALKENYL AMIDINE DERIVATIVE; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; OXIDATION; REDUCTION; SYNTHESIS;

AMIDINES; CATALYSIS; COPPER; CYCLIZATION; MOLECULAR STRUCTURE;

EID: 84863230228     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2120629     Document Type: Article

References (77)

1. Thomas, G. L.; Johannes, C. W. Curr. Opin. Chem. Biol. 2011, 15, 516
2. Tohme, R.; Darwiche, N.; Gali-Muhtasib, H. Molecules 2011, 16, 9665
3. Dandapani, S.; Marcaurelle, L. A. Curr. Opin. Chem. Biol. 2010, 14, 362
4. Welsch, M. E.; Snyder, S. A.; Stockwell, B. R. Curr. Opin. Chem. Biol. 2010, 14, 347
5. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337
6. Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A., Eds.; Elsevier: Oxford, 2008; Vol. 20 and others in this series.
7. Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Pergamon: Oxford, 2008.
8. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Pergamon: Oxford, 2008.
9. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; McKillop, A., Eds.; Pergamon: Oxford, 1996, and references therein.
10. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles; Wiley-VCH: Weinheim, 2003.
11. Toh, K. K.; Wang, Y.-F.; Ng, E. P. J; Chiba, S. J. Am. Chem. Soc. 2011, 133, 13942
12. Zhang, L.; Ang, G. Y.; Chiba, S. Org. Lett. 2010, 12, 3682
13. Chiba, S.; Zhang, L.; Lee, J.-Y. J. Am. Chem. Soc. 2010, 132, 7266
14. Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 11088
15. Wang, H.; Wang, Y.; Liang, D.; Liu, L.; Zhang, J.; Zhu, Q. Angew. Chem., Int. Ed. 2011, 50, 5678
16. Wang, J.; Wang, J.; Zhu, Y.; Lu, P.; Wang, Y. Chem. Commun. 2011, 47, 3275
17. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068
18. Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28
19. Ueda, S.; Nagasawa, H. J. Org. Chem. 2009, 74, 4272
20. Hewgley, J. B.; Stahl, S. S.; Kozlowski, M. C. J. Am. Chem. Soc. 2008, 130, 12232
21. Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932
22. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
23. Caron, S.; Wei, L.; Douville, J.; Ghosh, A. J. Org. Chem. 2010, 75, 945 and references therein
24. Cardona, F.; Goti, A. Nature Chem. 2009, 1, 269
25. de Figueiredo, R. M. Angew. Chem., Int. Ed. 2009, 48, 1190
26. Sibbald, P. A.; Michael, F. E. Org. Lett. 2009, 11, 1147
27. Hövelmann, C. H.; Streuff, J.; Brelot, L.; Muñiz, K. Chem. Commun. 2008, 2334
28. Muñiz, K.; Streuff, J.; Chávez, P.; Hövelmann, C. H. Chem. Asian J. 2008, 3, 1248
29. Muñiz, K.; Hövelmann, C. H.; Campos-Gómez, E.; Barluenga, J.; González, J. M.; Streuff, J.; Nieger, M. Chem. Asian J. 2008, 3, 776
30. Muñiz, K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763
31. Muñiz, K. J. Am. Chem. Soc. 2007, 129, 14542
32. Muñiz, K.; Streuff, J.; Hövelmann, C. H.; Núñez, A. Angew. Chem., Int. Ed. 2007, 46, 7125
33. Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586
34. Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308
35. Iglesias, A.; Muñiz, K. Chem.-Eur. J. 2009, 15, 10563
36. Li, H.; Widenhoefer, R. A. Org. Lett. 2009, 11, 2671
37. Sequeira, F. C.; Turnpenny, B. W.; Chemler, S. R. Angew. Chem., Int. Ed. 2010, 49, 6365
38. Zabawa, T. P.; Chemler, S. R. Org. Lett. 2007, 9, 2035
39. Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250
40. Zhao, B.; Peng, X.; Zhu, Y.; Ramirez, T. A.; Cornwall, R. G.; Shi, Y. J. Am. Chem. Soc. 2011, 133, 20890
41. Zhao, B.; Peng, X.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 11009
42. Wen, Y.; Zhao, B.; Shi, Y. Org. Lett. 2009, 11, 2365
43. Zhao, B.; Du, H.; Shi, Y. Org. Lett. 2008, 10, 1087
44. Zhao, B.; Yuan, W.; Du, H.; Shi, Y. Org. Lett. 2007, 9, 4943
45. Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589
46. Zhao, B.; Du, H.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 3523
47. Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 11688
48. Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762
49. Han, J.; Li, T.; Pan, Y.; Kattuboina, A.; Li, G. Chem. Biol. Drug Des. 2008, 71, 71
50. Timmons, C.; Mcpherson, L. M.; Chen, D.; Wei, H.-X.; Li, G. J. Peptide Res. 2005, 66, 249
51. Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777
52. Wei, H.-X.; Siruta, S.; Li, G. Tetrahedron Lett. 2002, 43, 3809
53. Li, G.; Wei, H.-X.; Kim, S. H.; Carducci, M. D. Angew. Chem., Int. Ed. 2001, 40, 4277
54. Röben, C.; Souto, J. A.; González, Y.; Lishchynskyi, A.; Muñiz, K. Angew. Chem., Int. Ed. 2011, 50, 9478
55. Li, H.; Widenhoefer, R. A. Tetrahedron 2010, 66, 4827
56. Booker-Milburn, K. I.; Guly, D. J.; Cox, B.; Procopiou, P. A. Org. Lett. 2003, 5, 3313
57. Liebeskind, L. S.; Yang, H.; Li, H. Angew. Chem., Int. Ed. 2009, 48, 1417
58. Villalobos, J. M.; Srogl, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 15734
59. Lebel, H.; Parmentier, M. Pure Appl. Chem. 2010, 82, 1827
60. Xu, Q.; Appella, D. H. Org. Lett. 2008, 10, 1497
61. Lebel, H.; Lectard, S.; Parmentier, M. Org. Lett. 2007, 9, 4797
62. Gillespie, K. M.; Crust, E. J.; Deeth, R. J.; Scott, P. Chem. Commun. 2001, 785
63. Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013
64. Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889
65. For a review on synthesis of sulfoxyimine using nitrene species, see: Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482
66. Rolff, M.; Tuczek, F. Angew. Chem., Int. Ed. 2008, 47, 2344
67. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047
68. Gamez, P.; Aubel, P. G.; Driessen, W. L.; Reedijk, J. Chem. Soc. Rev. 2001, 30, 376
69. Fontecave, M.; Pierre, J.-L. Coord. Chem. Rev. 1998, 170, 125
70. Kizirian, J.-C. Chem. Rev. 2008, 108, 140
71. Kotti, S. R. S. S.; Timmons, C.; Li, G. Chem. Biol. Drug Des. 2006, 67, 101
72. Viso, A.; de la Pradilla, R. F.; García, A.; Flores, A. Chem. Rev. 2005, 105, 3167
73. Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580
74. These cyclic amidines resisted to hydrolysis by acid and base. For reports on hydrolysis of cyclic amidine derivatives by hydrolysis for preparation of vicinal diamines, see: Jung, S.-H.; Kohn, H. J. Am. Chem. Soc. 1985, 107, 2931
75. Corey reported treatment of cyclic amidine with aluminium amalgam followed by aqueous acid provided vicinal diamine, see: Corey, E. J.; Kühnle, N. M. Tetrahedron Lett. 1997, 38, 8631
76. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464
77. 1-Azaspiro[4,5]decan-6-amine derivatives such as 8r have shown antinociceptive activity, see: Fujimoto, R. A.; Boxer, J.; Jackson, R. H.; Simke, J. P.; Neale, R. F.; Snowhill, E. W.; Barbas, B. J.; Williams, M.; Sills, M. A. J. Med. Chem. 1989, 32, 1259