Chemoselective isomerization of amide-substituted oxetanes with Lewis acid to give oxazine derivatives or bicyclic amide acetals

Abstract

The Lewis-acid catalyzed isomerization of secondary and tertiary amide-substituted oxetanes takes place chemoselectively, giving 5-hydroxymethyl-5,6-dihydro-4H-1,3-oxazines and reactive amide acetals consisting of a bicyclo[2.2.2]octane skeleton, respectively.

References

1. M. P. Dreyfuss and P. Dreyfuss, in Encyclopedia of Polymer Science and Engineering, Wiley, New York, 1987, vol. 10, pp. 653–670.
2. H. Ogawa, T. Hosomi, T. Kosaka, S. Kanoh, A. Ueyama and M. Motoi, Bull. Chem. Soc. Jpn., 1997, 70, 175; M. Motoi, S. Sekizawa, K. Asakura and S. Kanoh, Polym. J., 1993, 25, 1283 and references cited therein.
3. E. J. Corey and N. Raju, Tetrahedron Lett., 1983, 24, 5571; P. Ducray, H. Lamotte and B. Rousseau, Synthesis, 1997, 404.
4. S. Kanoh, T. Hashiba, K. Ando, H. Ogawa and M. Motoi, Synthesis, 1997, in the press.
5. T. Gajda and A. Zwierzak, Synthesis, 1981, 1005.
6. R. Feinauer, Synthesis, 1971, 16.
7. C. Lu and G. Odian, J. Polym. Sci., Part A: Polym. Chem., 1994, 32, 2283.
8. W. Seeliger, E. Aufderhaar, W. Diepers, R. Feinauer, R. Nehring, W. Thier and H. Hellmann, Angew. Chem., Int. Ed. Engl., 1966, 5, 875 and references cited therein; Y. Ito, Y. Inubushi, M. Zenbayashi, S. Tomita and T. Saegusa, J. Am. Chem. Soc., 1973, 95, 4447.