Copper-catalyzed cyclization and azidation of γ,δ-unsaturated ketone O-benzoyl oximes

Advanced Synthesis and Catalysis

Volumn 357, Issue 1, 2015, Pages 64-70

  Su, Hailin ^a   Li, Weifei ^a   Xuan, Zhaoli ^a   Yu, Wei ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Azidation; Copper catalysis; Cyclization; Dihydropyrroles; G,d unsaturated o benzoyl ketoximes

Indexed keywords

EID: 84920854741     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400681     Document Type: Article

References (72)

1. a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772;
2. Angew. Chem. Int. Ed. 1998, 37, 2580-2627;
3. b) F. Cardona, A. Goti, Nat. Chem. 2009, 1, 269-275;
4. c) R. M. de Figueiredo, Angew. Chem. 2009, 121, 1212-1215;
5. Angew. Chem. Int. Ed. 2009, 48, 1190-1193;
6. d) S. D. Jong, D. G. Nosal, D. J. Wardrop-Duncan, Tetrahedron 2012, 68, 4067-4105;
7. e) K. Muñiz, C. Martínez, J. Org. Chem. 2013, 78, 2168-2174.
8. Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 6312-6313;
9. b) H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 11688-11689;
10. c) H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2008, 130, 8590-8591;
11. d) B. Wang, H. Du, Y. Shi, Angew. Chem. 2008, 120, 8348-8351;
12. Angew. Chem. Int. Ed. 2008, 47, 8224-8227;
13. e) B. Zhao, H. Du, Y. Shi, J. Org. Chem. 2009, 74, 8392-8395;
14. f) B. Zhao, X. Peng, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 11009-11011;
15. g) R. G. Cornwall, B. Zhao, Y. Shi, Org. Lett. 2013, 15, 796-799;
16. h) B. Zhang, A. Studer, Org. Lett. 2014, 16, 1790-1793.
17. a) J. Streuff, C. H. Hovelmann, M. Nieger, K. Muñiz, J. Am. Chem. Soc. 2005, 127, 14586-14587;
18. b) P. A. Sibbald, F. E. Michael, Org. Lett. 2009, 11, 1147-1149.
19. K. Muñiz, J. Streuff, C. H. Hövelmann, A. Núlñez, Angew. Chem. 2007, 119, 7255-7258;
20. Angew. Chem. Int. Ed. 2007, 46, 7125-7127.
21. A. Iglesias, K. Muñiz, Chem. Eur. J. 2009, 15, 10563-10569.
22. a) T. P. Zabawa, D. Kasi, S. R. Chemler, J. Am. Chem. Soc. 2005, 127, 11250-11251;
23. b) F. C. Sequeira, B. W. Turnpenny, S. R. Chemler, Angew. Chem. 2010, 122, 6509-6512;
24. Angew. Chem. Int. Ed. 2010, 49, 6365-6368;
25. c) B. W. Turnpenny, S. R. Chemler, Chem. Sci. 2014, 5, 1786-1793.
26. a) K. Narasaka, M. Kitamura, Chem. Rec. 2002, 2, 268-277;
27. b) K. Narasaka, M. Kitamura, Eur. J. Org. Chem. 2005, 4505-4519;
28. c) F. W. Patureau, F. Glorius, Angew. Chem. 2011, 123, 2021-2023;
29. Angew. Chem. Int. Ed. 2011, 50, 1977-1979;
30. d) G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651-3678.
31. a) S. Liu, Y. Yu, L. S. Liebeskind, Org. Lett. 2007, 9, 1947-1950;
32. b) S. Liu, L. S. Liebeskind, J. Am. Chem. Soc. 2008, 130, 6918-6919;
33. c) P. C. Too, S. H. Chua, S. H. Wong, S. Chiba, J. Org. Chem. 2011, 76, 6159-6168;
34. d) Z.-H. Ren, Z.-Y. Zhang, B.-Q. Yang, Y.-Y. Wang, Z.-H. Guan, Org. Lett. 2011, 13, 5394-5397;
35. e) A. John, K. M. Nicholas, Organometallics 2012, 31, 7914-7920;
36. f) Y. Wei, N. Yoshikai, J. Am. Chem. Soc. 2013, 135, 3756-3759;
37. g) H. Liang, Z.-H. Ren, Y.-Y. Wang, Z.-H. Guan, Chem. Eur. J. 2013, 19, 9789-9794;
38. h) H. Huang, X. Ji, X. Tang, M. Zhang, X. Li, H. Jiang, Org. Lett. 2013, 15, 6254-6257;
39. i) Q. Wu, Y. Zhang, S. Cui, Org. Lett. 2014, 16, 1350-1353.
40. a) M. Noack, R. Gottlich, Chem. Commun. 2002, 536-537;
41. b) N. Matsuda, K. Hirano, K. T. Satoh, M. Miura, Angew. Chem. 2012, 124, 11997-12001;
42. Angew. Chem. Int. Ed. 2012, 51, 11827-11831;
43. c) N. Matsuda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2013, 135, 4934-4937.
44. a) Y. Koganemaru, M. Kitamura, K. Narasaka, Chem. Lett. 2002, 784-785;
45. b) K. Tanaka, M. Kitamura, K. Narasaka, Bull. Chem. Soc. Jpn. 2005, 78, 1659-1664.
46. a) E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368;
47. b) S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320-5374;
48. Angew. Chem. Int. Ed. 2005, 44, 5188-5240;
49. c) Organic Azides: Syntheses and Applications, (Eds.: S. Bräse, K. Banert), John Wiley & Sons, Ltd., 2010.
50. a) P. Panchaud, L. Chabaud, Y. Landais, C. Ollivier, P. Renaud, S. Zigmantas, Chem. Eur. J. 2004, 10, 3606-3614;
51. b) W. Song, S. I. Kozhushkov, L. Ackermann, Angew. Chem. Int. Ed. 2013, 52, 6576-6578.
52. a) T. Harschneck, S. Hummel, S. F. Kirsch, P. Klahn, Chem. Eur. J. 2012, 18, 1187-1193;
53. b) C. Tang, N. Jiao, J. Am. Chem. Soc. 2012, 134, 18924-18927;
54. c) D. Lubriks, I. Sokolovs, E. Suna, J. Am. Chem. Soc. 2012, 134, 15436-15442;
55. d) K. Matcha, R. Narayan, A. P. Antonchick, Angew. Chem. Int. Ed. 2013, 52, 7985-7989;
56. e) Q.-H. Deng, T. Bleith, H. Wadepohl, L. H. Gade, J. Am. Chem. Soc. 2013, 135, 5356-5359;
57. f) L. Zhu, H. Yu, Z. Xu, X. Jiang, L. Lin, R. Wang, Org. Lett. 2014, 16, 1562-1565;
58. g) H. Yin, T. Wang, N. Jiao, Org. Lett. 2014, 16, 2302-2305;
59. h) Z. Liu, P. Liao, X. Bi, Org. Lett. 2014, 16, 3668-3671.
60. [8,10]
61. a) A. Faulkner, J. F. Bower, Angew. Chem. 2012, 124, 1707-1711;
62. Angew. Chem. Int. Ed. 2012, 51, 1675-1679;
63. b) A. Faulkner, J. S. Scott, J. F. Bower, Chem. Commun. 2013, 49, 1521-1523;
64. c) N. J. Race, J. F. Bower, Org. Lett. 2013, 15, 4616-4619.
65. d)A. Faulkner, N. J. Race, J. S. Scott, J. F. Bower, Chem. Sci. 2014, 5. 2416-2421.
66. M. Kitamura, K. Narasaka, Bull. Chem. Soc. Jpn. 2008, 81, 539-547.
67. S. Chiba, Bull. Chem. Soc. Jpn. 2013, 86, 1400-1411.
68. D. E. Mancheno, A. R. Thornton, A. H. Stoll, A. Kong, S. B. Blakey, Org. Lett. 2010, 12, 4030-4033.
69. D. Schuch, P. Fries, M. Dönges, B. M. Pérez, J. Hartung, J. Am. Chem. Soc. 2009, 131, 12918-12920.
70. W. Li, P. Jia, B. Han, D. Li, W. Yu, Tetrahedron 2013, 69, 3274-3280.
71. th edn., Springer, Heidelberg, Berlin, 2007, p 427.
72. A control experiment indicates that performing the reaction under an argon atmosphere has little effect for other substrates.