A catalyst-free N-H insertion/Mannich-type reaction cascade of α-nitrodiazoesters

Tetrahedron Letters

Volumn 54, Issue 32, 2013, Pages 4159-4163

  Yang, Ting ^a   Zhuang, Hao ^b   Lin, Xichen ^a   Xiang, Jia Ning ^a   Elliott, John D ^a   Liu, Lianghui ^c   Ren, Feng ^a  

^a GLAXOSMITHKLINE   (China)

^b SHANGHAI JIAO TONG UNIVERSITY   (China)

^c PEKING UNIVERSITY   (China)

Author keywords

Amino aryl ester; Nitrodiazo ester; Carbene; Catalyst free reaction; Mannich type reaction; N H insertion

Indexed keywords

ANILINE; CARBENE; ESTER DERIVATIVE; HYDROGEN; NITROGEN; SOLVENT;

ARTICLE; CATALYST; MANNICH REACTION; SUBSTITUTION REACTION; TEMPERATURE;

EID: 84879845673     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.05.131     Document Type: Article

References (41)

1. For reviews: H.M.L. Davies, and R.E.J. Beckwith Chem. Rev. 103 2003 2861
2. S.F. Zhou, and Q.L. Zhou Acc. Chem. Res. 45 2012 1365
3. X. Zhao, Y. Zhang, and J. Wang Chem. Commun. 2012 10162
4. H.M.L. Davies, and D. Morton Chem. Soc. Rev. 2011 1857 40
5. S. France, and L.H. Phun Curr. Org. Synth. 7 2010 332
6. C.N. Slattery, A. Ford, and A.R. Maguire Tetrahedron 66 2010 6681
7. H.M.L. Davies, and J.R. Denton Chem. Soc. Rev. 38 2009 3061
8. A. Padwa Chem. Soc. Rev. 38 2009 3072
9. Y. Zhang, and J. Wang Chem. Commun. 2009 5350
10. Z. Zhang, and J. Wang Tetrahedron 64 2008 6577
11. C.J. Moody Angew. Chem., Int. Ed. 46 2007 9148
12. For examples: X. Xu, P.Y. Zavalij, and M.P. Doyle Angew. Chem., Int. Ed. 51 2012 9829
13. M.C. McMills, R.J. Humes, and O.M. Pavlyuk Tetrahedron Lett. 53 2012 849
14. T. Osako, D. Panichakul, and Y. Uozumi Org. Lett. 14 2012 194
15. S.F. Zhu, B. Xu, G.-P. Wang, and Q.L. Zhou J. Am. Chem. Soc. 134 2012 436
16. B. Xu, S.-F. Zhu, X.-L. Xie, J.-J. Shen, and Q.-L. Zhou Angew. Chem., Int. Ed. 50 2011 11483
17. S.F. Zhu, X.-G. Song, Y. Li, Y. Cai, and Q.-L. Zhou J. Am. Chem. Soc. 132 2010 16374
18. J.R. Denton, and H.M.L. Davies Org. Lett. 11 2009 787
19. C.-Y. Zhou, J.C. Wang, J. Wei, Z.-J. Xu, Z. Guo, K.-H. Low, and C.-M. Che Angew. Chem., Int. Ed. 51 2012 11376
20. For recent reviews on organocatalysis: S.J. Connon Chem. Commun. 2008 2499
21. S.J. Connon Synlett 2009 354
22. P. Melchiorre Angew. Chem., Int. Ed. 51 2012 9748
23. F. Giacalone, M. Gruttadauria, P. Agrigento, and R. Noto Chem. Soc. Rev. 41 2012 2406
24. S.S. So, and A.E. Mattson J. Am. Chem. Soc. 134 2012 8798
25. S.S. So, T.J. Auvil, V.J. Garza, and A.E. Mattson Org. Lett. 14 2012 444
26. An enantioselective organocatalytic N-H insertion: H. Saito, D. Morita, T. Uchiyama, M. Miyake, and S. Miyairi Tetrahedron Lett. 53 2012 6662
27. For examples of carbene generation from α-nitro-α-diazo carbonyl compounds, see: U. Shollkopf, and P. Tonne Leibigs Ann. Chem. 753 1971 135
28. P.E. O'Bannon, and W.P. Dailey Tetrahedron Lett. 29 1988 5719
29. P.E. O'Bannon, and W.P. Dailey J. Org. Chem. 54 1989 3096
30. A.B. Charette, R.P. Wurz, and T. Ollevier Helv. Chim. Acta 85 2002 4468
31. R.P. Wurz, and A.B. Charette J. Org. Chem. 69 2004 1262
32. S. Zhu, J.A. Perman, and X.P. Zhange Angew. Chem., Int. Ed. 47 2008 8460
33. V.N. Lindsay, W. Lin, and A.B. Charette J. Am. Chem. Soc. 131 2009 16383
34. S.F. Vanier, G. Larouche, R.P. Wurz, and A.B. Charette Org. Lett. 12 2010 672
35. L. Bernardi, M. Fochi, M.C. Franchini, and A. Ricci Org. Biomol. Chem. 10 2012 2911
36. R.R. Knowles, and E.N. Jacobsen Proc. Natl. Acad. Sci. U.S.A. 107 2010 20678
37. J. Aleman, A. Parra, H. Jiang, and K.A. Jorgensen Chem. Eur. J. 17 2011 6890
38. S.H. Gellmann Chem. Rev. 97 1997 Special issue on molecular recognition
39. A similar structure was used as organocatalysis: G. Suez, V. Bloch, G. Nisnevich, and M. Gandelman Eur. J. Org. Chem. 2012 2118
40. E. Aller, R.T. Buck, M.J. Drysdale, L. Ferris, D. Haigh, C.J. Moody, N.D. Pearson, and J.B. Sanghera J. Chem. Soc., Perkin Trans. 1 1996 2879
41. S.R. Hansen, J.E. Spangler, J.H. Hansen, and H.M.L. Davies Org. Lett. 14 2012 4626