Diazo compounds as electrophiles to react with 1,4-dilithio-1,3-dienes: Efficient synthesis of 1-imino-pyrrole derivatives

Organic Letters

Volumn 15, Issue 16, 2013, Pages 4182-4185

  Zhan, Ming ^a   Zhang, Shaoguang ^a   Zhang, Wen Xiong ^a   Xi, Zhenfeng ^a,b  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882755340     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401878q     Document Type: Article

References (55)

1. Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091
2. Doyle, M. P.; Mckervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998.
3. Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577
4. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2012, 46, 236
5. Doyle, M. P. Chem. Rev. 1986, 86, 919
6. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223
7. Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50
8. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
9. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
10. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704
11. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863
12. Zhang, Y.; Wang, J. Chem. Commun. 2009, 5350
13. Takamura, N.; Mizoguchi, T.; Yamada, S. Tetrahedron Lett. 1973, 14, 4267
14. Takamura, N.; Yamada, S. Chem. Pharm. Bull. 1976, 24, 800
15. Yasui, E.; Wada, M.; Takamura, N. Tetrahedron Lett. 2006, 47, 743
16. Yasui, E.; Wada, M.; Takamura, N. Tetrahedron 2009, 65, 461
17. Li, W.; Liu, X.; Hao, X.; Hu, X.; Chu, Y.; Cao, W.; Qin, S.; Hu, C.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2011, 133, 15268
18. Xi, Z.; Zhang, W.-X. Synlett 2008, 2557
19. Xi, Z. Acc. Chem. Res. 2010, 43, 1342
20. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002.
21. The Chemistry of Organolithium Compounds; Rappoport, Z.; Marek, I., Eds; Wiley: Chichester, 2004.
22. Xi, Z.; Song, Q. J. Org. Chem. 2000, 65, 9157
23. Song, Q.; Chen, J.; Jin, X.; Xi, Z. J. Am. Chem. Soc. 2001, 123, 10419
24. Liu, L.; Zhang, W.-X.; Wang, C.; Wang, C. Y.; Xi, Z. Angew. Chem., Int. Ed. 2009, 48, 8111
25. Xi, Z. Sci. China, Ser. B 2009, 39, 1115
26. Zhang, S.; Wei, J.; Zhan, M.; Luo, Q.; Wang, C.; Zhang, W.-X.; Xi, Z. J. Am. Chem. Soc. 2012, 134, 11964
27. Platon, M.; Amardeil, R.; Djakovitch, L.; Hierso, J.-C. Chem. Soc. Rev. 2012, 41, 3929
28. Inman, M.; Moody, C. J. Chem. Sci. 2013, 4, 29
29. Bell, I.; Madroñero, R.; Whiting, M. C. J. Chem. Soc. 1958, 3195
30. Amon, M.; Ligneau, X.; Schwartz, J.-C.; Stark, H. Bioorg. Med. Chem. Lett. 2006, 16, 1938
31. Ferorelli, S.; Abate, C.; Colabufo, N. A.; Niso, M.; Inglese, C.; Berardi, F.; Perrone, R. J. Med. Chem. 2007, 50, 4648
32. Christl, M.; Lesch, S.; Deuerlein, S.; Stalke, D. Helv. Chim. Acta 2005, 88, 1421
33. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231
34. Klimenko, I. P.; Medvedev, A. F.; Korolev, V. A.; Kolomnikova, G. D.; Tomilov, Y. V.; Bubnov, Y. N. J. Organomet. Chem. 2009, 694, 2106
35. Wang, D. H.; Liu, Q.; Chen, B.; Zhang, L. P.; Tung, C. H.; Wu, L. Z. Chin. Sci. Bull. 2010, 55, 2855
36. Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748
37. Wooten, A.; Carroll, P. J.; Maestri, A. G.; Walsh, P. J. J. Am. Chem. Soc. 2006, 128, 4624
38. Guerrero, A.; Hughes, D. L.; Bochmann, M. Organometallics 2006, 25, 1525
39. Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802
40. Sarazin, Y.; Wright, J. A.; Harding, D. A. J.; Martin, E.; Woodman, T. J.; Hughes, D. L.; Bochmann, M. J. Organomet. Chem. 2008, 693, 1494
41. Merkel, S.; Stern, D.; Stalke, D. Angew. Chem., Int. Ed. 2009, 48, 6350
42. Clegg, W.; Conway, B.; Garcia-Alvarez, P.; Kennedy, A. R.; Klett, J.; Mulvey, R. E.; Russo, L. Dalton Trans. 2010, 39, 62
43. MacIntosh, I. S.; Sherren, C. N.; Robertson, K. N.; Masuda, J. D.; Pye, C. C.; Clyburne, J. A. C. Organometallics 2010, 29, 2063
44. Schmidt, S.; Schulz, S.; Bläser, D.; Boese, R.; Bolte, M. Organometallics 2010, 29, 6097
45. Zhou, Y.; Zhang, W.-X.; Xi, Z. Organometallics 2012, 31, 5546
46. Seyferth, D.; Womack, G. B.; Archer, C. M.; Dewan, J. C. Organometallics 1989, 8, 430
47. Gunnoe, T. B.; White, P. S.; Templeton, J. L. Organometallics 1997, 16, 3794
48. Bailey, P. J.; Liddle, S. T.; Morrison, C. A.; Parsons, S. Angew. Chem., Int. Ed. 2001, 40, 4463
49. Li, X.; Baldamus, J.; Nishiura, M.; Tardif, O.; Hou, Z. Angew. Chem., Int. Ed. 2006, 45, 8184
50. Lichtenberg, C.; Jochmann, P.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2011, 50, 5753
51. Lichtenberg, C.; Engel, J.; Spaniol, T. P.; Englert, U.; Raabe, G.; Okuda, J. J. Am. Chem. Soc. 2012, 134, 9805
52. Ménard, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 4409
53. Peterson, J. K.; MacDonald, M. R.; Ziller, J. W.; Evans, W. J. Organometallics 2013, 32, 2625
54. Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101
55. Ernst, R. D.; Freeman, J. W.; Swepston, P. N.; Wilson, D. R. J. Organomet. Chem. 1991, 402, 17