Regiospecific ficini [2 + 2] cycloaddition of ynamides with cyclic isoimidium salts under catalyst-free conditions

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4316-4319

  Yuan, Yini ^a   Bai, Lu ^a   Nan, Jiang ^a   Liu, Jingjing ^a   Luan, Xinjun ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMIDE; DOPASTIN; INORGANIC SALT;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; AMIDES; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; SALTS; STEREOISOMERISM;

EID: 84906223300     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5020587     Document Type: Article

References (50)

1. Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485
2. Godula, K.; Sames, D. Science 2006, 312, 67
3. Dembitsky, V. M. J. Nat. Med. 2008, 62, 1
4. Liu, R.; Zhang, M.; Wyche, T. P.; Winston-McPherson, G. N.; Bugni, T. S.; Tang, W. Angew. Chem., Int. Ed. 2012, 51, 7503
5. Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507
6. Basler, B.; Schuster, O.; Bach, T. J. Org. Chem. 2005, 70, 9798
7. Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681
8. Fürstner, A.; Schlecker, A.; Lehmann, C. W. Chem. Commun. 2007, 41, 4277
9. Treutwein, J.; Hilt, G. Angew. Chem., Int. Ed. 2008, 47, 6811
10. Jo, H.; Fitzgerald, M. E.; Winkler, J. D. Org. Lett. 2009, 11, 1685
11. López-Carrillo, V.; Echavarren, A. M. J. Am. Chem. Soc. 2010, 132, 9292
12. Aikawa, K.; Hioki, Y.; Shimizu, N.; Mikami, K. J. Am. Chem. Soc. 2011, 133, 20092
13. Nishimura, A.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2012, 134, 15692
14. de Nanteuil, F.; Waser, J. Angew. Chem., Int. Ed. 2013, 52, 9009
15. For a seminal review, see: Ficini, J. Tetrahedron 1976, 32, 1449
16. Ficini, J.; Krief, A. Tetrahedron Lett. 1969, 10, 1431
17. Ficini, J.; Touzin, A. M. Tetrahedron Lett. 1972, 13, 2093
18. Ficini, J.; Touzin, A. M. Tetrahedron Lett. 1974, 15, 1447
19. Ficini, J.; Falou, S.; d'Angelo, J. Tetrahedron Lett. 1977, 18, 1931
20. Ficini, J.; Krief, A.; Guingant, A.; Desmaele, D. Tetrahedron Lett. 1981, 22, 725
21. Ficini, J.; Guingant, A.; d'Angelo, J.; Stork, G. Tetrahedron Lett. 1983, 24, 907
22. Ficini, J.; Desmaele, D.; Touzin, A. M. Tetrahedron Lett. 1983, 24, 1025
23. Zaugg, H. E.; Swett, L. R.; Stone, G. R. J. Org. Chem. 1958, 23, 1389
24. Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455
25. Dekorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
26. Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840
27. Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681
28. Villeneuve, K.; Riddell, N.; Tam, W. Tetrahedron 2006, 62, 3823
29. Kohnen, A. L.; Mak, X. Y.; Lam, T. Y.; Dunetz, J. R.; Danheiser, R. L. Tetrahedron 2006, 62, 3815
30. Wang, Y. P.; Danheiser, R. L. Tetrahedron Lett. 2011, 52, 2111
31. Hsung, R. P.; Zificsak, C. A.; Wei, L. L.; Douglas, C. J.; Xiong, H.; Mulder, J. A. Org. Lett. 1999, 1, 1237
32. Kurtz, K. C. M.; Hsung, R. P.; Zhang, Y. Org. Lett. 2005, 8, 231
33. You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li, G.; Lu, T.; Hsung, R. P. Synlett 2007, 1656
34. Pirwerdjan, R.; Priebbenow, D. L.; Becker, P.; Lamers, P.; Bolm, C. Org. Lett. 2013, 15, 5397
35. Shindoh, N.; Takemoto, Y.; Takasu, K. Chem. - Eur. J. 2009, 15, 7026
36. Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547
37. Li, H.; Hsung, R. P.; Dekorver, K. A.; Wei, Y. Org. Lett. 2010, 12, 3780
38. Schotes, C.; Mezzetti, A. Angew. Chem., Int. Ed. 2011, 50, 3072
39. Schotes, C.; Althaus, M.; Aardoom, R.; Mezzetti, A. J. Am. Chem. Soc. 2012, 134, 1331
40. Schotes, C.; Bigler, R.; Mezzetti, A. Synthesis 2012, 44, 513
41. Smith, D. L.; Chidipudi, S. R.; Goundry, W. R.; Lam, H. W. Org. Lett. 2012, 14, 4934
42. Boyd, G. V. Chem. Commun. 1969, 1147
43. Boyd, G. V.; Monteil, R. L. J. Chem. Soc., Perkin Trans. 1 1978, 1338
44. Baydar, A. E.; Boyd, G. V. J. Chem. Soc., Perkin Trans. 1 1978, 1360
45. Baydar, A. E.; Boyd, G. V. J. Chem. Soc., Perkin Trans. 1 1981, 2871
46. Baydar, A. E.; Boyd, G. V.; Aupers, J.; Lindley, P. F. J. Chem. Soc., Perkin Trans. 1 1981, 2890
47. Balaban, A. R.; Balaban, T. S.; Boyd, G. V. Synthesis 1987, 577
48. Boeckman, R. K., Jr.; Miller, Y.; Ryder, T. R. Org. Lett. 2010, 12, 4524
49. Ficini, J.; Eman, A.; Touzin, A. M. Tetrahedron Lett. 1976, 17, 679
50. Ficini, J.; Duréault, A. Tetrahedron Lett. 1977, 18, 809