A novel synthesis of α- and β-morpholino enones by electron transfer sensitized photooxidation of 2-morpholinocyclopropanols

Abstract

An electron transfer mechanism is proposed to account for the photooxidation of 2-morpholinocyclopropanols 1 to the amino enone derivatives 2 and 3 in the presence of 9,10-dicyanoanthracene or triphenylpyrylium tetrafluoroborate and triplet oxygen.

References

1. P. C. Wong and D. R. Arnold, Tetrahedron Lett., 1979, 23, 2101; S. B. Karki, J. P. Dinnocenzo, S. Farid, J. L. Goodman, I. R. Gould and T. A. Zona, J. Am. Chem. Soc., 1997, 119, 431.
2. T. Tamai, K. Mizuno, I. Hashida and Y. Otsuji, J. Org. Chem., 1992, 57, 5338 and references cited therein.
3. K. Mizuno, N. Kamiyama, N. Ichinose and Y. Otsuji, Tetrahedron, 1985, 41, 2207.
4. K. Gollnick and U. Paulmann, J. Org. Chem., 1990, 55, 5954; K. Gollnick, X.-L. Xiao and U. Paulmann, J. Org. Chem., 1990, 55, 5945.
5. F. Algarra, M. V. Baldovi, H. Garcia, M. A. Miranda and J. Primo, Tetrahedron, 1993, 47, 10 897.
6. (a) W. Weigel, G. Reck, S. Schiller and H.-G. Henning, Tetrahedron Lett., 1993, 34, 6737; (b) W. Weigel, S. Schiller and H.-G. Henning, Tetrahedron, 1997, 53, 7855; (c) W. Weigel and P. J. Wagner, J. Am. Chem. Soc., 1996, 118, 12 858.
7. N. H. Cromwell, J. Am. Chem. Soc., 1940, 62, 2897; F. Felluga, P. Nitta, G. Pitacco and E. Valentin, J. Chem. Soc., Perkin Trans. 1, 1971, 1648.
8. D. Rehm and A. Weller, Ber. Bunsenges. Phys. Chem., 1969, 73, 834.
9. P. E. Correa, G. Hardy and D. P. Riley, J. Org. Chem., 1988, 53, 1695.
10. M. A. Miranda and H. Garcia, Chem. Rev., 1994, 94, 1063.
11. R. Akaba, H. Sakuragi and K. Tokumaru, Chem. Phys. Lett., 1990, 174, 80.
12. G. Haucke, P. Czerney and F. Cebulla, Ber. Bunsenges. Phys. Chem., 1992, 96, 880.
13. G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401.
14. E. Brunner, Ber. Bunsenges. Phys. Chem., 1968, 68, 468; A. P. Schaap, K. A. Kaklika and L. Kaskar, J. Am. Chem. Soc., 1980, 102, 389.
15. H. J. Kuhn, S. E. Braslavsky and R. Schmidt, Pure Appl. Chem., 1989, 2, 187.
16. K. Mizuno, N. Ichinose and Y. Otsuji, J. Org. Chem., 1992, 57, 1855; K. Okada, K. Hisamitsu and T. Mukai, Tetrahedron Lett., 1981, 22, 1251.