Copper-catalyzed synthesis of α-amino imides from tertiary amines: Ugi-type three-component assemblies involving direct functionalization of sp3 C-Hs adjacent to nitrogen atoms

Organic Letters

Volumn 12, Issue 19, 2010, Pages 4240-4243

  Ye, Xin ^a   Xie, Chunsong ^a   Pan, Yuanyuan ^a   Han, Laihong ^a   Xie, Tian ^a  

^a HANGZHOU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; COPPER; IMIDE; NITROGEN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINES; CATALYSIS; COPPER; IMIDES; MOLECULAR STRUCTURE; NITROGEN;

EID: 77957113130     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101576q     Document Type: Article

References (64)

1. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123
2. Weber, L. Curr. Med. Chem. 2002, 9, 2085
3. Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51
4. Iden, H. S.; Lubell, W. D. J. Comb. Chem. 2008, 10, 691
5. Cuny, G.; Bois-Choussy, M.; Zhu, J. P. J. Am. Chem. Soc. 2004, 126, 14475
6. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138
7. Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2006, 45, 7230
8. Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582
9. Zhu, M. K.; Xu, X. Y.; Gong, L. Z. Adv. Synth. Catal. 2008, 350, 1390
10. Yu, Z. P.; Liu, X. H.; Zhou, L.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2009, 48, 5195
11. Bacchi, A.; Pelagatti, P.; Pelizzi, C.; Rogolino, D. J. Organomet. Chem. 2009, 694, 3200
12. Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 14988
13. Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8
14. Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168
15. Domling, A. Chem. Rev. 2006, 106, 17
16. Isaacson, J.; Kobayashi, Y. Angew. Chem., Int. Ed. 2009, 48, 1845
17. Pan, S. C.; List, B. Angew. Chem., Int. Ed. 2008, 47, 3622
18. Chapman, T. M.; Davies, I. G.; Gu, B. H.; Block, T. M.; Scopes, D. I. C.; Hay, P. A.; Courtney, S. M.; McNeill, L. A.; Schofield, C. J.; Davis, B. G. J. Am. Chem. Soc. 2005, 127, 506
19. Kaim, L. E.; Grimaud, L.; Oble, J. Angew. Chem., Int. Ed. 2005, 44, 7961
20. Ugi, I.; Cornelius, S. Chem. Ber. 1961, 94, 734
21. McFarland, J. W. J. Org. Chem. 1963, 28, 2179
22. Kreutzkamp, N.; Lammerhirt, K. Angew. Chem., Int. Ed. 1968, 7, 372
23. Giovenzana, G. B.; Tron, G. C.; Paola, S. D.; Menegotto, I. G.; Pirali, T. Angew. Chem., Int. Ed. 2006, 45, 1099
24. Diorazio, L. J.; Motherwell, W. B.; Sheppard, T. D.; Waller, R. B. Synlett 2006, 2281
25. Tanaka, Y.; Hasui, T.; Suginome, M. Org. Lett. 2007, 9, 4407
26. Ngouansavanh, T.; Zhu, J. P. Angew. Chem., Int. Ed. 2006, 45, 3495
27. Brioche, J.; Masson, G.; Zhu, J. P. Org. Lett. 2010, 12, 1432
28. Ngouansavanh, T.; Zhu, J. P. Angew. Chem., Int. Ed. 2007, 46, 5775
29. Rodolphe, J.; Julien, H.; Alice, R.; Julien, S.-K.; Olivier, B. Chem.Eur. J. 2010, 16, 2654
30. Chen, H. Y.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995
31. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507
32. Godula, K.; Sames, D. Science 2006, 312, 67
33. Bergman, R. G. Nature 2007, 446, 391
34. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439
35. Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061
36. Whited, M. T.; Grubbs, R. H. Acc. Chem. Res. 2009, 42, 1607
37. Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094
38. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
39. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704
40. Thu, H.-Y.; Tong, G. S. M.; Huang, J. S.; Chan, S. L. F.; Deng, Q. H.; Che, C. M. Angew. Chem., Int. Ed. 2008, 47, 9747
41. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
42. Badiei, Y. M.; Dinescu, A.; Dai, X. L.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961
43. Wurtele, C.; Sander, O.; Lutz, V.; Waitz, T.; Tuczek, F.; Schindler, S. J. Am. Chem. Soc. 2009, 131, 7544
44. Lucas, H. R.; Li, L.; Sarjeant, A. A. N.; Vance, M. A.; Solomon, E. I.; Karlin, K. D. J. Am. Chem. Soc. 2009, 131, 3230
45. Balcells, D.; Raynaud, C.; Crabtree, R. H.; Eisenstein, O. Chem. Commun. 2009, 1772
46. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
47. Wasa, M.; Engle, K. M.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 9886
48. Murarka, S.; Deb, I.; Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 13226
49. Roesky, P. W. Angew. Chem., Int. Ed. 2009, 48, 4892
50. Kubiak, R.; Prochnow, I.; Doye, S. Angew. Chem., Int. Ed. 2009, 48, 1153
51. Sud, A.; Sureshkumar, D.; Klussmann, M. Chem. Commun. 2009, 3169
52. Tsuchikama, K.; Kasagawa, M.; Endo, K.; Shibata, T. Org. Lett. 2009, 11, 1821
53. Li, Y. Z.; Li, B. J.; Lu, X. Y.; Lin, S.; Shi, Z. J. Angew. Chem., Int. Ed. 2009, 48, 3817
54. Li, C. J. Acc. Chem. Res. 2009, 42, 335
55. Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810
56. Baslé, O.; Li, C. J. Green Chem. 2007, 9, 1047
57. Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 6968
58. Li, Z. P.; Bohle, D. S.; Li, C. J. Proc. Nat. Acad. Sci. 2006, 103, 8928
59. Zhang, Y. M.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Org. Lett. 2007, 9, 3813
60. Baslé, O.; Li, C. J. Chem. Commun. 2009, 4124
61. Huang, L. H.; Zhang, X. B.; Zhang, Y. H. Org. Lett. 2009, 11, 3730
62. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
63. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
64. Similar transfer of acyls to the nitrogens of isonitriles had already been reported in ref 7b and the following reference: Ugi, I.; Steinbruckner, C. Chem. Ber. 1961, 94, 2802