Intramolecular aziridination: Decomposition of diazoamides with tethered imino bonds

Organic Letters

Volumn 1, Issue 4, 1999, Pages 667-670

  Wright, Dennis L ^a,b   McMills, Mark C ^a  

^a OHIO UNIVERSITY   (United States)

^b University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000694934     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990750h     Document Type: Article

References (42)

1. (1)(a) McMills, M. C.; Wright, D. L.; Zubkowski, J.; Valente, E. Tetrahedron Lett. 1996, 37, 7205-7208.
2. (b) Aziridine substrates derived from diazoketones have been reported as minor reaction products. Padwa, A.; Dean, D. C. J. Org. Chem. 1990, 55, 405.
3. (c) Padwa, A.; Dean, D. C.; Osterhout, M. H.; Precede, L.; Semones, M. A. J. Org. Chem. 1994, 59, 5347.
4. For alternative approaches to aziridination from alkene substrates, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744-6
5. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-9
6. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
7. (d) Bergmeier, S. C.; Seth, P. P. J. Org. Chem. 1997, 62, 2671-2674.
8. (e) Dubois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. Acc. Chem. Res. 1997, 30, 364-372.
9. (f) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744-6746.
10. (g) Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309-312.
11. (h) Atkinson, R. S.; Fawcett, J.; Russell, D. R.; Tughan, G. J. Chem. Commun. 1986, 832-834.
12. (i) Atkinson, R. S.; Gattrell, W. T.; Ayscough, A. P.; Raynham, T. M. Chem. Commun. 1996, 1935-1936.
13. (j) Harm, A. M.; Knight, J. G.; Stemp, G. Synlett 1996, 677.
14. (k) Hogale, M. B.; Shelar, A. R.; Chavan, P. B. Indian J. Chem., Sect. B 1992, 31, 456-458.
15. (l) Jacobsen, E. N.; Li, Z.; Protopopova, M. Abstracts of Papers, 205th National Meeting of the American Chemical Society, Denver, CO; American Chemical Society: Washington, DC, 1993; Abstract 137-ORGN.
16. (m) Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. J. Chem. Soc., Perkin Trans. 2 1988, 1517-1524.
17. (n) Vedejs, E.; Sano, H. Tetrahedron Lett. 1992, 33, 3261-3264.
18. (o) Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586-1587.
19. For approaches to aziridination of imines, see: (a) Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed Engl. 1995, 34, 676.
20. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-7
21. (c) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889-10.
22. (d) Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. Phosphorus, Sulfur Silicon Relat. Elem. 1997, 120, 361.
23. (e) Dekimpe, N.; Desmaele, D. Tetrahedron Lett. 1994, 35, 8023.
24. (f) Mohan, J. M.; Uphade, B. S.; Choudhary, V. R.; Ravindranathan, T.; Sudalai, A. Chem. Commun. 1997, 1429.
25. (g) Rasmussen, K. G.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1997, 1287.
26. (h) Wang, D. K.; Dai, L. X.; Hou, X. L. Chem. Commun. 1997, 1231.
27. (i) Wipf, P.; Miller C. P. Tetrahedron Lett. 1992, 33, 6267.
28. (j) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
29. Moran, M.; Bernardinelli, G.; Muller, P. Helv. Chim. Acta 1995, 78, 2048.
30. Curphey, T. J. J. Org. Chem. 1979, 44, 2805.
31. Davies, H. M. L.; Cantrell, W. R.; Romines, K. R.; Baum, J. S. In Organic Synthesis; Meyers, A. I., Ed.; 1991; Vol. 70, p 93.
32. Aziridine nitrogen bearing electronegative heteroatoms possess high barriers to inversion, see: (a) Schurig, V., Leyrer, U. Tetrahedron: Asymmetry 1990, 1, 865.
33. (b) Atkinson, R. S., Williams, P. J. J. Chem. Soc., Perkin Trans. 2 1996, 205.
34. (c) Kost D., Raban, M. J. Am. Chem. Soc. 1982, 104, 2960. The products of systems in this study show no tendency to interconvert N-O stereochemistry.
35. The trans relationship at the bridgeheads was assigned by the small coupling constant between the two bridgehead protons and with analogy to compound 10.
36. Marino, J. P.; Osterhout, M. H.; Price, A. T.; Sheehan, S. M.; Padwa, A. Tetrahedron Lett. 1994, 35, 849.
37. The structure was confirmed by X-ray crystallographic analysis. The coordinates have been deposited with the Cambridge Crystallographic Database.
38. A similar pathway has been suggested for the spontaneous formation of triazoles. Hunig, S.; Kraft, P. Heterocycles 1995, 40, 639.
39. We have observed an analogous cycloaddition with a similarly disposed olefin to produce a simple pyrazole. This structure was confirmed by X-ray crystallography. Weekly, R. M. Masters Thesis, Ohio University, 1997. See also: Doyle, M. P.; Kalinin, A. V. J. Org. Chem. 1996, 61, 2179. Doyle, M. P.; Dorow, R. L.; Tamblyn, W. H. J. Org. Chem. 1982, 47, 4059. equation presented
40. We have observed an analogous cycloaddition with a similarly disposed olefin to produce a simple pyrazole. This structure was confirmed by X-ray crystallography. Weekly, R. M. Masters Thesis, Ohio University, 1997. See also: Doyle, M. P.; Kalinin, A. V. J. Org. Chem. 1996, 61, 2179. Doyle, M. P.; Dorow, R. L.; Tamblyn, W. H. J. Org. Chem. 1982, 47, 4059. equation presented
41. For a related approach to the mitomycins, see (a) Jones, G. B.; Moody, C. J. Chem. Commun.. 1988, 1009.
42. (b) Jones, G. B.; Moody, C. J.; Padwa, A.; Kassir, J. M. J. Chem. Soc., Perkin Trans. 1 1991, 1, 1721.