Cobalt-catalyzed efficient aziridination of alkenes

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3191-3193

  Gao, Guang Yao ^a   Harden, Jeremiah D ^a   Zhang, X Peter ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23044479258     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050896i     Document Type: Article

References (43)

1. (a) Hu, X. E. Tetrahedron 2004, 60, 2701.
2. (b) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
3. (c) Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93.
4. (d) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
5. (e) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
6. (a) Muller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
7. (b) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, p 607.
8. (c) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
9. (a) Dauban, P.; Dodd, R. H. Synlett 2003, 1571.
10. (b) Koser, G. F. Top. Curr. Chem. 2003, 224, 137.
11. (c) Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett. 1975, 361.
12. For the use of in situ formed iminoiodane, see: (a) Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233.
13. (b) Dauban, P.; Saniere, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
14. (c) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672.
15. (a) Simkhovich, L.; Gross, Z. Tetrahedron Lett. 2001, 42, 8089.
16. (b) Albone, D. P.; Aujla, P. S.; Taylor, P. C.; Challenger, S.; Derrick, A. M. J. Org. Chem. 1998, 63, 9569.
17. (c) Mairena, M. A.; Diaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. Organometallics 2004, 23, 253.
18. (a) Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30.
19. (b) Antunes, A. M. M.; Marto, S. J. M.; Branco, P. S.; Prabhakar, S.; Lobo, A. M. Chem. Commun. 2001, 405.
20. (a) Omura, K.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Commun. 2004, 2060.
21. (b) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
22. For selected examples, see: (a) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
23. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
24. A recent addition to the catalyst series is a Ag complex of a substituted terpyridine ligand: Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
25. The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000-2003; Vols. 1-20.
26. (a) Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073.
27. (b) Mansuy, D.; Mahy, J.-P.; Dureault, A.; Bedi, G.; Battioni, P. J. Chem. Soc., Chem. Commun. 1984, 1161.
28. (a) Mahy, J.-P.; Bedi, G.; Battioni, P.; Mansuy, D. J. Chem. Soc., Perkin Trans. 2 1988, 1517.
29. (b) Lai, T.-S.; Kwong, H.-L.; Che, C.-M.; Peng, S.-M. Chem. Commun. 1997, 2373.
30. (c) Simonato, J.-P.; Pecaut, J.; Scheldt, W. R.; Marchon, J.-C. Chem. Commun. 1997, 989.
31. (d) Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. J. Am. Chem. Soc. 1999, 121, 9120.
32. (e) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem. Eur. J. 2002, 8, 1563.
33. (a) Chen, Y.; Huang, L.; Ranade, M. A.; Zhang, X. P. J. Org. Chem. 2003, 68, 3714.
34. (b) Chen, Y.; Huang, L.; Zhang, X. P. J. Org. Chem. 2003, 68, 5925.
35. (c) Chen, Y.; Huang, L.; Zhang, X. P. Org. Lett. 2003, 5, 2493.
36. (d) Huang, L.; Chen, Y.; Gao, G.-Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 8179.
37. (e) Lee, M.-Y.; Chen, Y.; Zhang, X. P. Organometallics 2003, 22, 4905.
38. (f) Chen, Y.; Zhang, X. P. J. Org. Chem. 2004, 69, 2431
39. (g) Vyas, R.; Gao, G.-Y.; Harden, J. D.; Zhang, X. P. Org. Lett. 2004, 6, 1907.
40. (h) Chen, Y.; Fields, K. B.; Zhang, X. P. J. Am. Chem. Soc. 2004, 126, 14178.
41. For cobalt porphyrin-mediated amination with aryl azides, see: Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Gotti, C. L.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem. Eur. J. 2003, 9, 249.
42. 2 was shown to catalyze aziridination of styrene with bromine-T to form the desired aziridine in 56% yield when excess styrene was used (styrene/bromamine-T = 5:1). See ref 6a.
43. Co(TPP) was previously found to catalyze aziridination of styrene with bromine-T to form the desired aziridine in 27% yield when excess styrene was used (styrene/bromamine-T = 5:1). See ref 13a.