Δ2-isoxazolines from β,γ-unsaturated oximes

Journal of Heterocyclic Chemistry

Volumn 43, Issue 3, 2006, Pages 535-539

  Mosher, Michael D ^a   Emmerich, Laura G ^a   Frost, Katherine S ^a   Anderson, Benjamin ^a  

^a UNIVERSITY OF NEBRASKA AT KEARNEY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLINE DERIVATIVE; OXIME DERIVATIVE; PALLADIUM;

ADDITION REACTION; ARTICLE; CARBONYLATION; CATALYSIS; CYCLIZATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 33744998168     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430303     Document Type: Article

References (37)

1. J. B. Lubetsky, A. Dios, J. Han, B. Aljabari, B. Ruzsicska, R. Mitchell, E. Lolis and Y. Al-Abed, J. Biological Chem., 277(28), 24976 (2002).
2. th ACS National Meeting, Anaheim, CA, 2004.
3. [3a] C. B. Xue, J. Wityak, T. M. Sielecki, D. J. Pinto, D. G. Batt, G. A. Cain, M. Sworin, A. L. Rockwell, J. J. Roderick, S. Wang, M. J. Orwat, W. E. Frietze, L. L. Bostrom, J. Liu, C. A. Higley, F. W. Rankin, A. E. Tobin, G. Emmett, G. K. Lalka, J. Y. Sze, S. V. DiMeo, S. A. Mousa, M. J. Thoolen, A. L. Racanelli, E. A. Hausner, T. M. Reilly, W. F. DeGrado, R. R. Wexler and R. E. Olson, J. Med. Chem., 40, 2064 (1997); and
4. [3b] J. Wityak, T. M. Sielecki, D. J. Pinto, G. Emmett, J. Y. Sze, J. Liu, A. E. Tobin, S. Wang, B. Jiang, P. Ma, S. A. Mousa, R. R. Wexler and R. E. Olson, J. Med. Chem., 40, 50 (1997).
5. H. Zhang, W. H. Chan, A. W. M. Lee, P. F. Xia, W. Y. Wong, Lett. Org. Chem., 1, 66 (2004).
6. H. Alper, F. W. Hartstock and B. Despeyroux, Chem. Commun., 905 (1984).
7. G. Zeni and R. C. Larock, Chem. Rev., 104, 2285 (2004);
8. J.-L. Malleron, J.-C. Fiaud and J.-Y. Legros, Handbook of Palladium-Catalyzed Organic Reactions, Academic Press, New York, NY, 2000;
9. J. Tsuji, Palladium Reagents and Catalysts, John Wiley and Sons, New York, NY, 1995.
10. For leading references, see: [a] R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 113, 6689 (1991);
11. [b] R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 60, 3270 (1995);
12. [c] T. Pei, and R. A. Widenhoefer, J. Am. Chem. Soc. 123, 11290 (2001);
13. [d] T. Pei, and R. A. Widenhoefer, Chem. Commun., 650 (2002);
14. [e] R. D. Walkup, and M. D. Mosher, Tetrahedron 41, 9285 (1993);
15. [f] R. D. Walkup, and M. D. Mosher, Tetrahedron Lett., 35, 8545 (1994);
16. [g] E. J. Stoner, B. A. Roden, and S. Chembrukar, Tetrahedron Lett., 38, 4981 (1997);
17. [h] Y. Tamaru, M. Hojo, and Z. Yoshida, J. Org. Chem., 56, 1099 (1991);
18. [i] S. Cacchi, G. Fabrizi, and L. Moro, Tetrahedron Lett., 39, 5101 (1998) and references therein;
19. [j] R. D. Walkup, L. Guan, M. D. Mosher, S. W. Kim, and Y. S. Kim, Synlett, 88 (1993);
20. [k] W. F. J. Karstens, F. P. J. T. Rutjes, and H. Hiemstra, Tetrahedron Lett., 38, 6275 (1997).
21. [8a] R. D. Walkup and G. Park, Tetrahedron Lett., 29, 5505 (1988);
22. [b] R. D. Walkup and G. Park, J. Am. Chem. Soc., 112, 1597 (1990);
23. [c] T. Gallagher, I. W. Davies, S. W. Jones, D. Lathbury, M. F. Mahon, K. C. Molloy, R. W. Shaw and P. Vernon, J. Chem. Soc., Perkin 1., 433 (1992);
24. [d] S. D. Burke and L. Jiang, Org. Lett., 3, 1953 (2001);
25. [e] P. S. Baran and E. J. Corey, J. Am. Chem. Soc., 124, 7904 (2002).
26. S. Eicher, The Chemistry of the Carbonyl Group, S. Patai, ed., John Wiley and Sons, New York, NY, 1970, pp 621-693.
27. R. M. Coates, P. D. Senter and W. R. Baker, J. Org. Chem., 47, 3597 (1982).
28. M. D. Mosher and S. Meisenbach, The Chem. Educ., 7(6), 356 (2002).
29. J. S. Cowie, P. D. Landor and S. D. Landor, J. Chem. Soc., Perkin 1, 720 (1973).
30. T. Satoh, T. Itaya, K. Okuro, M. Miura and M. Nomura, J. Org. Chem., 60, 7267 (1995).
31. S. Hanessian and P. Lavallee, Can. J. Chem., 53, 2975 (1975).
32. [15a] G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 60, 4462 (1968);
33. [b] C. L. Liotta and H. P. Harris, J. Am. Chem. Soc., 96, 2250 (1974).
34. [16a] K. Maeda, T. Hosokawa, S.-I. Murahashi and I. Moritani, Tetrahedron Lett., 14, 5075 (1973);
35. [b] T. Hosokawa, N. Shimo, K. Maeda, A. Sonoda, and S.-I. Murahashi, Tetrahedron Lett., 17, 383 (1976).
36. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 43, 2923 (1978).
37. H. Grund and V. Jaeger, J. Chem. Res., Synopses, 2, 54 (1979).