N-bromoimide/DBU combination as a new strategy for intermolecular allylic amination

Organic Letters

Volumn 15, Issue 20, 2013, Pages 5186-5189

  Wei, Ying ^a   Liang, Fushun ^a   Zhang, Xintong ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 DIAZABICYCLO(5.4.0)UNDEC 7 ENE; 1,8-DIAZABICYCLO(5.4.0)UNDEC-7-ENE; ALKENE; ALLYL COMPOUND; AMINE; FUSED HETEROCYCLIC RINGS; N BROMOSUCCINIMIDE;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; ALLYL COMPOUNDS; AMINATION; AMINES; BICYCLO COMPOUNDS, HETEROCYCLIC; BROMOSUCCINIMIDE; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 84886313737     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402287n     Document Type: Article

References (61)

1. Brown, E. G. Ring Nitrogen and Key Biomolecules; Springer: Boston, MA, 1998.
2. Hili, R.; Yudin, A. K. Nat. Chem. Biol. 2006, 2, 284
3. Henkel, T.; Brunne, R. M.; Müller, H.; Reichel, F. Angew. Chem., Int. Ed. 1999, 38, 643
4. Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762
5. Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496
6. Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316
7. Du, H.; Zhao, B.; Yian, S. J. Am. Chem. Soc. 2008, 130, 8590
8. Liu, G.; Yin, G.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733
9. Wang, B.; Du, H.; Shi, Y. Angew. Chem., Int. Ed. 2008, 47, 8224
10. Reed, S. A.; Mazzotti, A. R.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11701
11. Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11707
12. Fu, R.; Zhao, B.; Shi, Y. J. Org. Chem. 2009, 74, 7577
13. Yin, G.; Wu, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 11978
14. McDonald, R. I.; Stahl, S. S. Angew. Chem., Int. Ed. 2010, 49, 5529
15. Ramirez, T. A.; Zhao, B.; Shi, Y. Chem. Soc. Rev. 2012, 41, 931
16. Weinstein, A. B.; Stahl, S. S. Angew. Chem., Int. Ed. 2012, 51, 11505
17. Takada, H.; Nishibayashi, Y.; Ohe, K.; Uemura, S.; Baird, C. P.; Sparey, T. J.; Taylor, P. C. J. Org. Chem. 1997, 62, 6512
18. Smith, K.; Hupp, C. D.; Allen, K. L.; Slough, G. A. Organometallics 2005, 24, 1747
19. Clark, J. S.; Roche, C. Chem. Commun. 2005, 5175
20. Srivastava, R. S.; Bertrand, R., III; Gallo, A. A.; Nicholas, K. M. Tetrahedron Lett. 2011, 52, 3478
21. Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689
22. Liu, Y.; Che, C.-M. Chem.-Eur. J. 2010, 16, 10494
23. Huang, D.; Wang, H.; Xue, F.; Shi, Y. J. Org. Chem. 2011, 76, 7269
24. Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036
25. Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742
26. Parker, K. A.; Chang, W. Org. Lett. 2003, 5, 3891
27. Parker, K. A.; Chang, W. Org. Lett. 2005, 7, 1785
28. Zalatan, D. N.; DuBois, J. J. Am. Chem. Soc. 2007, 129, 7242
29. Skucas, E.; Kong, J. R.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 9220
30. Wipf, P.; Kendal, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761
31. Kakuuchi, A.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 2003, 44, 923
32. Kochi, T.; Ellman, J. A. J. Am. Chem. Soc. 2004, 126, 15652
33. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941
34. Xie, Y.; Hu, J.; Wang, Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613
35. Sharpless, K. B.; Hori, T.; Truesdale, L. K.; Dietrich, C. O. J. Am. Chem. Soc. 1976, 98, 269
36. Bruncko, M.; Khuong, T. A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 454
37. Souto, J. A.; Zian, D.; Muñiz, K. J. Am. Chem. Soc. 2012, 134, 7242
38. Trillo, P.; Baeza, A.; Nájera, C. J. Org. Chem. 2012, 77, 7344
39. Wei, Y.; Lin, S.; Liang, F. Org. Lett. 2012, 14, 4202
40. Wei, Y.; Lin, S.; Liang, F.; Zhang, J. Org. Lett. 2013, 15, 852
41. Wei, Y.; Lin, S.; Zhang, J.; Niu, Z.; Fu, Q.; Liang, F. Chem. Commun. 2011, 47, 12394
42. Wei, Y.; Lin, S.; Xue, H.; Liang, F.; Zhao, B. Org. Lett. 2012, 14, 712
43. Xue, H.; Tan, H.; Wei, D.; Wei, Y.; Lin, S.; Liang, F.; Zhao, B. RSC Adv. 2013, 3, 5382
44. Castellote, I.; Morön, M.; Burgos, C.; Alvarez-Builla, J.; Martin, A.; Gomez-Sal, P.; Vaquero, J. J. Chem. Commun. 2007, 1281
45. Crowston, E. H.; Lobo, A. M.; Prabhakar, S.; Rzepa, H. S.; Williams, D. J. Chem. Commun. 1984, 276
46. Raatikainen, K.; Rissanen, K. Chem. Sci. 2012, 3, 1235
47. Wang, Y.-M.; Wu, J.; Hoong, C.; Rauniyar, V.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 12928
48. Examples with an imido moiety from NBS or NBP itself as the N -nucleophile are scarce. For a recent example, see: Alix, A.; Lalli, C.; Retailleau, P.; Masson, G. J. Am. Chem. Soc. 2012, 134, 10389
49. Koppel, I.; Koppel, J.; Degerbeck, F.; Grehn, L.; Ragnarsson, U. J. Org. Chem. 1991, 56, 7172
50. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456
51. Cotton, F. A.; Stokely, P. F. J. Am. Chem. Soc. 2012, 92, 294
52. Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem., Int. Ed. 2012, 51, 10938
53. Sakakura, A.; Ukai, A.; Ishihara, K. Nature 2007, 445, 900
54. Snyder, S. A.; Treitler, D. S. Angew. Chem., Int. Ed. 2009, 48, 7899
55. Cui, X.-L.; Brown, R. S. J. Org. Chem. 2000, 65, 5653
56. Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20655
57. Cheng, Y. A.; Chen, T.; Tan, C. K.; Heng, J. J.; Yeung, Y.-Y. J. Am. Chem. Soc. 2012, 134, 16492
58. Chen, F.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2013, 135, 1232
59. Tan, C. K.; Yeung, Y.-Y. Chem. Commun. 2013, 49, 7985
60. Trofimov, A.; Chernyak, N.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 13538
61. Li, Z.; Gevorgyan, V. Angew. Chem., Int. Ed. 2011, 50, 2808