Remarkably efficient olefin aziridination mediated by a new copper(II) complex

Organometallics

Volumn 18, Issue 26, 1999, Pages 5435-5437

  Halfen, Jason A ^a   Hallman, Jason K ^a   Schultz, John A ^a   Emerson, Joseph P ^a  

^a UNIVERSITY OF WISCONSIN EAU CLAIRE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000553187     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9908579     Document Type: Article

References (31)

1. (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 35, 599.
2. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: Oxford, U.K., 1996; Vol. 1A, pp 1-60.
3. (c) Rai, K. M. L.; Hassner, A. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: Oxford, U.K., 1996; Vol. 1A, pp 61-96.
4. For example, consider Mitomycin C and Azinomycins A and B, recent syntheses of which are respectively described in the following two publications: Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Coleman, R. S.; Kong, J.-S. J. Am. Chem. Soc. 1998, 120, 3538-3539.
5. For example, consider Mitomycin C and Azinomycins A and B, recent syntheses of which are respectively described in the following two publications: Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Coleman, R. S.; Kong, J.-S. J. Am. Chem. Soc. 1998, 120, 3538-3539.
6. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744-6746.
7. (b) Perez, P. J.; Brookhart, M.; Templeton, J. L. Organometallics 1993, 12, 261-262.
8. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753.
9. (d) Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 676-678.
10. (e) Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7090-7091.
11. (f) Casarrubois, L.; Perez, J. A.; Brookhart, M.; Templeton, J. L. J. Org. Chem. 1996, 61, 8358-8359.
12. (g) Mayer, M. P.; Hossain, M. M. J. Org. Chem. 1998, 63, 6839-6844.
13. (a) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5327.
14. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329.
15. (c) Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469-471.
16. (d) Rasmusseen, K. G.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 1995, 1401-1402.
17. (e) Antilla, J. C.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 5099-5100.
18. (f) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, pp 113-151.
19. (g) Sodegren, M. J.; Alonso, D. A.; Andersson, P. G. Tetrahedron: Asymmetry 1997, 8, 3563-3566.
20. Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett. 1975, 361-362.
21. (a) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752-10765.
22. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Rouden, J. J. Org. Chem. 1994, 59, 4037-4039.
23. (a) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889-5890.
24. (b) Diaz-Requejo, M. M.; Perez, P. J.; Brookhart, M.; Templeton, J. L. Organometallics 1997, 16, 4399-4402.
25. Haselhorst, G.; Stoetzel, S.; Strassburger, A.; Walz, W.; Wieghardt, K.; Nuber, B. J. Chem. Soc., Dalton Trans. 1993, 83-90.
26. Full synthetic details and characterization data are provided as Supporting Information.
27. 3 groups.
28. Halfen, J. A.; Tolman, W. B. J. Am. Chem. Soc. 1994, 116, 5475-5476.
29. The cis stereochemistry of the aziridine derived from cyclooctene, N-tosyl-9-azabicyclo[6.1.0]nonane, was confirmed by X-ray crystallography: Emerson, J. P.; Halfen, J. A. Unpublished results.
30. A catalyst loading of 5 mol % 1 vs PhINTs was used in order to expedite completion of these rather sluggish reactions.
31. Takada, H.; Nishibayashi, Y.; Ohe, K.; Uemura, S.; Baird, C. P.; Sparey, T. J.; Taylor, P. C. J. Org. Chem. 1997, 62, 6512-6518.