An efficient ring-opening reaction of aziridines with alkynes catalyzed by CuOTf

Synlett

Volumn , Issue 10, 2004, Pages 1691-1694

  Ding, Chang Hua ^b   Dai, Li Xin ^a   Hou, Xue Long ^a,b  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkynylation; Aziridines; Copper(I) triflate; Lewis acids; Ring opening reaction

Indexed keywords

ALKYNE; AZIRIDINE DERIVATIVE; COPPER DERIVATIVE; OXYGEN;

ALKYNYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; RING OPENING;

EID: 4143102531     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829551     Document Type: Article

References (39)

1. (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
2. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
3. Kump, J. E. G. In Comprehensive Organic Synthesis, Vol. 7; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 467.
4. For examples of the reaction of aziridine with alcohols or phenols see: (a) Jacques, B.; Josette, C. R.; Roger, V. Synthesis 1992, 288. (b) Bellos, K.; Stamm, H. J. Org. Chem. 1995, 60, 5661. (c) Wipf, P.; Uto, Y. Tetrahedron Lett. 1999, 40, 5165. (d) Stamm, H.; Schneider, L. Chem. Ber. 1974, 107, 2870.
5. For examples of the reaction of aziridine with alcohols or phenols see: (a) Jacques, B.; Josette, C. R.; Roger, V. Synthesis 1992, 288. (b) Bellos, K.; Stamm, H. J. Org. Chem. 1995, 60, 5661. (c) Wipf, P.; Uto, Y. Tetrahedron Lett. 1999, 40, 5165. (d) Stamm, H.; Schneider, L. Chem. Ber. 1974, 107, 2870.
6. For examples of the reaction of aziridine with alcohols or phenols see: (a) Jacques, B.; Josette, C. R.; Roger, V. Synthesis 1992, 288. (b) Bellos, K.; Stamm, H. J. Org. Chem. 1995, 60, 5661. (c) Wipf, P.; Uto, Y. Tetrahedron Lett. 1999, 40, 5165. (d) Stamm, H.; Schneider, L. Chem. Ber. 1974, 107, 2870.
7. For examples of the reaction of aziridine with alcohols or phenols see: (a) Jacques, B.; Josette, C. R.; Roger, V. Synthesis 1992, 288. (b) Bellos, K.; Stamm, H. J. Org. Chem. 1995, 60, 5661. (c) Wipf, P.; Uto, Y. Tetrahedron Lett. 1999, 40, 5165. (d) Stamm, H.; Schneider, L. Chem. Ber. 1974, 107, 2870.
8. For examples of the reaction of aziridine with thiols see: (a) Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784. (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253. (c) Bae, J. H.; Shin, S. H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041. (d) Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323. (e) Wu, J.; Hou, X. L.; Dai, L. X. J. Chem. Soc., Perkin Trans, 1 2001, 1314.
9. For examples of the reaction of aziridine with thiols see: (a) Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784. (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253. (c) Bae, J. H.; Shin, S. H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041. (d) Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323. (e) Wu, J.; Hou, X. L.; Dai, L. X. J. Chem. Soc., Perkin Trans, 1 2001, 1314.
10. For examples of the reaction of aziridine with thiols see: (a) Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784. (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253. (c) Bae, J. H.; Shin, S. H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041. (d) Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323. (e) Wu, J.; Hou, X. L.; Dai, L. X. J. Chem. Soc., Perkin Trans, 1 2001, 1314.
11. For examples of the reaction of aziridine with thiols see: (a) Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784. (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253. (c) Bae, J. H.; Shin, S. H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041. (d) Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323. (e) Wu, J.; Hou, X. L.; Dai, L. X. J. Chem. Soc., Perkin Trans, 1 2001, 1314.
12. For examples of the reaction of aziridine with thiols see: (a) Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784. (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253. (c) Bae, J. H.; Shin, S. H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041. (d) Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323. (e) Wu, J.; Hou, X. L.; Dai, L. X. J. Chem. Soc., Perkin Trans, 1 2001, 1314.
13. For examples of the reaction of aziridine with amines see: (a) Nakajima, K.; Tanaka, T.; Morita, K.; Okawa, K. Bull. Chem. Soc. Jpn. 1980, 53, 283. (b) Meguro, M.; Yamamoto, Y. Heterocycles 1996, 43, 2473. (c) Lucet, D.; Gallo, T. L.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580. (d) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
14. For examples of the reaction of aziridine with amines see: (a) Nakajima, K.; Tanaka, T.; Morita, K.; Okawa, K. Bull. Chem. Soc. Jpn. 1980, 53, 283. (b) Meguro, M.; Yamamoto, Y. Heterocycles 1996, 43, 2473. (c) Lucet, D.; Gallo, T. L.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580. (d) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
15. For examples of the reaction of aziridine with amines see: (a) Nakajima, K.; Tanaka, T.; Morita, K.; Okawa, K. Bull. Chem. Soc. Jpn. 1980, 53, 283. (b) Meguro, M.; Yamamoto, Y. Heterocycles 1996, 43, 2473. (c) Lucet, D.; Gallo, T. L.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580. (d) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
16. For examples of the reaction of aziridine with amines see: (a) Nakajima, K.; Tanaka, T.; Morita, K.; Okawa, K. Bull. Chem. Soc. Jpn. 1980, 53, 283. (b) Meguro, M.; Yamamoto, Y. Heterocycles 1996, 43, 2473. (c) Lucet, D.; Gallo, T. L.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580. (d) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
17. (a) Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204.
18. (b) Osborn, H. M.; Sweeney, J. B.; Howson, B. Synlett 1993, 675.
19. (c) Tanner, D.; He, H. M.; Somfai, P. Tetrahedron 1992, 48, 6069.
20. (d) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153.
21. (e) Lygo, B. Synlett 1993, 764.
22. (f) Dubois, L.; Mehta, A.; Tourette, E. J. Org. Chem. 1994, 59, 434.
23. (g) Bouayed, Z.; Chanet-Ray, J.; Ducher, S.; Vessiere, R. J. Heterocycl. Chem. 1991, 28, 1757.
24. (h) Müller, P.; Nury, P. Org. Lett. 1999, 1, 439.
25. (a) Gronquist, M. R.; Meinwald, J. J. Org. Chem. 2001, 66, 1075.
26. (b) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272.
27. (c) Daub, G. W.; Heering, D. A.; Overman, L. A. Tetrahedron 1988, 44, 3919.
28. (d) Compain, P.; Goré, J.; Vatèle, J. M. Tetrahedron 1996, 52, 10405.
29. (e) Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151.
30. (f) Ooi, T.; Kagoshima, N.; Ichikama, H.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3328.
31. (g) Fuji, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y. Heterocyde 1996, 42, 701.
32. (a) Li, A. H.; Dai, L. X.; Hou, X. L. Chem. Commun. 1996, 491.
33. (b) Li, A. H.; Dai, L. X.; Hou, X. L.; Chen, M. B. J. Org. Chem. 1996, 61, 4641.
34. (c) Wang, D. K.; Dai, L. X.; Hou, X. L. Chem. Commun. 1997, 1231.
35. (d) Li, A. H.; Zhou, Y. G.; Dai, L. X.; Hou, X. L.; Xia, L. J.; Lin, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 1317.
36. (e) Hou, X. L.; Yang, X. F.; Dai, L. X.; Chen, X. F. Chem. Commun. 1998, 747.
37. (f) Wu, J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2000, 65, 1344.
38. (g) Hou, X. L.; Fan, R. H.; Dai, L. X. J. Org. Chem. 2002, 67, 5295.
39. (h) Fan, R. H.; Hou, X. L. J. Org. Chem. 2003, 68, 726.