Site selectivity in the addition of ketoximes to activated aliènes and alkynes; N- versus O-alkylation

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 2, 1999, Pages 143-148

  Heaney, Frances ^a   Kelly, Bronvvyn M ^a   Bourke, Sharon ^a   Rooney, Oliver ^a   Cunningham, Desmond ^a   McArdle, Patrick ^a  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000970511     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808167k     Document Type: Article

References (43)

1. R. Grigg, F. Heaney, J. Markandu, S. Surendrakumar, M. Thornton-Pett and W. J. Warnock, Tetrahedron, 199I, 47, 4007;
2. A. Hassner, R. Maurya, A. Padwa and W. H. Bullock, J. Org. Chem., 1991,56,2775.
3. (a) R. Grigs, J. Markandu, T. Perrior, S. Surendrakumar and W. J. Warnock, Tetrahedron Lett., 1990, 31, 559;
4. (b) R. Grigg, J. Markandu, T. Perrior, S. Surendrakumar and W. J. Warnock, Tetrahedron, 1992, 47, 6929;
5. C. O'Mahony and F. Heaney, Chem. Commun., I996, 167.
6. R. Grigg, J. Markandu and S. Surendrakumar, Tetrahedron Lett., 1990, 31, 1191;
7. R. Grigg and J. Markandu, Tetrahedron Lett., 1989, 30, 5489;
8. R. Grigg, M. Hadjisoteriou, P. Kennewell, J. Markandu and M. Thornton-Pett, J. Chem. Soc., Chem. Commun., 1992, 1388;
9. R. Grigg, M. Hadjisoteriou, P. Kennewell and J. Markandu, J. Chem. Soc., Chem. Commun., 1992, 1537;
10. M. Frederickson, R. Grigg, J. Markandu and J. Redpath, J. Chem. Soc., Chem. Commun., 1994,2225;
11. H. A. Dondas, R. Grigg and C. S. Frampton, Tetrahedron Lett., 1997,38,5719.
12. R. Grigg, F. Heaney, S. Surendrakamar and W. J. Warnock, Tetrahedron, 1991,47,4477.
13. S. R. Landor, in The Chemistry of the Aliènes, cd. S. R. Länder, Academic Press, London, 1982, vol. 2, pp. 361-397;
14. H. F. Schuster and G. M. Coppola, Aliènes in Organic Synthesis, Wiley Interscience, New York, 1984;
15. P. Perlmutter, in Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series, Volume 9, Pergamon Press, Ltd., 1992.
16. J. March, Advanced Organic Chemistry, Wiley Interscience, New York, 1985, 3rd edn., pp. 664-672..
17. R. Grigg, T. R. Perrior, G. J. Sexton, S. Surendrakumar and T. Suzuki, J. Client. Soc., Client. Commun., 1993, 372.
18. M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Client. Soc., Perkin Trims. I, 1994, 3379.
19. G. A. Pinna, M. A. Pirisi and G.'Paglietti, J. Cliein. Res. (S), 1990, 360;
20. G. A. Pinna, M. A. Pirisi and G. Paglietti, J. Cliem. Res. (S), 1993,210;
21. S. E. Korostova, S. G. Shevchenko and V. V. Shcherbakov, Zh. Org. Khint, 1993, 29, 1639
22. (Cliem. Abstr., 1994, 121, 255563v);
23. V. Gômez, A. Pérez-Medrano and J. M. Muchowski, J. Org. Cliem., 1994, 59, 1219;
24. P. S. Branco, S. Prabhakar, A. M. Lobo and D. J. Williams, Tetrahedron, 1992,48,6335.
25. I. Yavari and A. Ramazani, Synth. Commun., 1997,27, 1449.
26. E. Winterfeldt and W. Krohn, Angcw. Cliem., Int. Ed. Engl., 1967,6, 709. .
27. R. Huisgen and M. Christi, Cliem. Ber., 1973,106, 3291.
28. (a) D. Lathbury and T. Gallagher, Tetrahedron Lett., 1985,26, 6249;
29. (b) D. Lathbury and T. Gallagher, J. Chcm. Sac., Cltem. Commun., 1986, 1017;
30. J. Grimaldi and A. Cormons, Tetrahedron Lett., 1985,26,825.
31. (a) R. W. Lang and H.-J. Hansen, Helv. Cliim. Ada, 1980, 63, 483;
32. (b) G. Buono and J. R. Llinas, J. Am. Client. Soc., 1981, 103, 4532;
33. K. N. Houk, in Per/cyclic Reactions, ed. A. March and R. E. Lehr, Academic Press, New York, 1977, vol. 11, p. 181;
34. A much improved synthetic route to allene-l,3-dicarboxylates has appeared during the preparation of this manuscript-M. Node, T. Fujiuara, S. Ichihashi and K. Nishide, Tetrahedron Lett., 1998,6331.
35. Y. Naruse, S. Katita and A. Tsunekawa, Synlett, 1995,711.
36. W. Verboom, E. O. M. Orlemans, H. J. Berga, M. W. Scheltinga and D. N. Rcinhoudt, Tetrahedron, 1986,42,5053;
37. M. S. El-Hossini, K. J. McCullough and G, R. Proctor, Tetrahedron Lett., 1986, 27, 3783.
38. 1,3-Dipolar cycloaddition to aliènes has been the subject of two recent reviews; A. Padwa, M. Meske and Z. Ni, Tetrahedron, 1995, 51,89;
39. G. Broggini and G. Zecch'i, Ga. Chint. lia!., 1996,126,479.
40. S. Blechert, Synthesis, 1989,71.
41. G. M. Sheldrick, Ada Crystallogr., Sect. A, 1990,46,467.
42. G. M. Sheldrick, SHELXL-97 a computer program for crystal structure determination, University of Göttingen, 1997.
43. P. McArdle, J. Appl. Crystallogr., 1995,28, 65.