Novel Tandem Conjugate Addition-Ramberg-Bäcklund Rearrangements

Synlett

Volumn 1997, Issue 9, 1997, Pages 1043-1044

  Evans, Paul ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002288838     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1540     Document Type: Article

References (25)

1. Ramberg, L.; Bäcklund, B. Ark. Kemi. Mineral. Geol. 1940, 27, Band 13A. 1 (Chem. Abstr., 1940, 34, 4725).
2. Ramberg, L.; Bäcklund, B. Ark. Kemi. Mineral. Geol. 1940, 27, Band 13A. 1 (Chem. Abstr., 1940, 34, 4725).
3. For reviews see Paquette, L. A. Org. React., 1977, 25, 1; Oae, S.; Uchida, Y. Chapter 12, pp. 649-664 and Braverman, S. Chapter 13, pp. 691-698, in The Chemistry of Sulphones and Sulphoxides, Eds. Patai, S.; Rappoport, Z.; Stirling, C. J. M., John Wiley, Chichester, 1988; Simpkins, N. S. Sulfones in Organic Synthesis, Pergamon Press, Oxford, 1993.
4. For reviews see Paquette, L. A. Org. React., 1977, 25, 1; Oae, S.; Uchida, Y. Chapter 12, pp. 649-664 and Braverman, S. Chapter 13, pp. 691-698, in The Chemistry of Sulphones and Sulphoxides, Eds. Patai, S.; Rappoport, Z.; Stirling, C. J. M., John Wiley, Chichester, 1988; Simpkins, N. S. Sulfones in Organic Synthesis, Pergamon Press, Oxford, 1993.
5. For reviews see Paquette, L. A. Org. React., 1977, 25, 1; Oae, S.; Uchida, Y. Chapter 12, pp. 649-664 and Braverman, S. Chapter 13, pp. 691-698, in The Chemistry of Sulphones and Sulphoxides, Eds. Patai, S.; Rappoport, Z.; Stirling, C. J. M., John Wiley, Chichester, 1988; Simpkins, N. S. Sulfones in Organic Synthesis, Pergamon Press, Oxford, 1993.
6. (a) Chen, T. B. R. A.; Burger, J. J.; de Waard, E. R. Tetrahedron Lett. 1977, 4527;
7. (b) Burger, J. J.; Chen, T. B. R. A.; de Waard, E. R.; Huisman, H. O. Tetrahedron 1981, 37, 417;
8. (c) Block, E.; Aslam, M.; Eswarakrishnan, V.; Gebreyes, K.; Hutchinson, J.; Iyer, R.; Laffitte, J.-A.; Wall, A. J. Am. Chem. Soc. 1986, 108, 4568.
9. Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, p. 880.
10. Grumann, A.; Marley, H.; Taylor, R. J. K. Tetrahedron Lett. 1995, 36, 7767.
11. See, for example, Casy , G.; Taylor, R. J. K. Tetrahedron 1989, 45, 455; Jeffery, S. M.; Sutherland, A. G.; Pyke, S. M.; Powell, A. K.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1993, 2317; Graham, A. E.; Loughlin, W. A.; Moore, M. H.; Pyke, S. M.; Wilson, G.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1996, 661; Gamble, M. P.; Giblin, G. M. P.; Montana, J. G.; O'Brien, P.; Ockendon, T. P.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7457.
12. See, for example, Casy , G.; Taylor, R. J. K. Tetrahedron 1989, 45, 455; Jeffery, S. M.; Sutherland, A. G.; Pyke, S. M.; Powell, A. K.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1993, 2317; Graham, A. E.; Loughlin, W. A.; Moore, M. H.; Pyke, S. M.; Wilson, G.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1996, 661; Gamble, M. P.; Giblin, G. M. P.; Montana, J. G.; O'Brien, P.; Ockendon, T. P.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7457.
13. See, for example, Casy , G.; Taylor, R. J. K. Tetrahedron 1989, 45, 455; Jeffery, S. M.; Sutherland, A. G.; Pyke, S. M.; Powell, A. K.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1993, 2317; Graham, A. E.; Loughlin, W. A.; Moore, M. H.; Pyke, S. M.; Wilson, G.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1996, 661; Gamble, M. P.; Giblin, G. M. P.; Montana, J. G.; O'Brien, P.; Ockendon, T. P.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7457.
14. See, for example, Casy , G.; Taylor, R. J. K. Tetrahedron 1989, 45, 455; Jeffery, S. M.; Sutherland, A. G.; Pyke, S. M.; Powell, A. K.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1993, 2317; Graham, A. E.; Loughlin, W. A.; Moore, M. H.; Pyke, S. M.; Wilson, G.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1996, 661; Gamble, M. P.; Giblin, G. M. P.; Montana, J. G.; O'Brien, P.; Ockendon, T. P.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7457.
15. Evans, P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 3055.
16. We have only found one reference to this type of overall transformation although it was carried out as a two step process and experimental details and yield were not given; the substrate was 1-bromo-1-(methylsulfonyl)ethene, indicating that non-activated substrates could be compatible with this methodology (footnote 6 in Clive, D. L. J.; Boivin, T. L. B. J. Org. Chem. 1989, 54, 1997).
17. For examples see Ueno, Y.; Khare, R. K.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1983, 2637; Boehme, H.; Lohmeyer, H.-D.; Wiekop, J. Liebigs Ann. 1954, 587, 51.
18. For examples see Ueno, Y.; Khare, R. K.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1983, 2637; Boehme, H.; Lohmeyer, H.-D.; Wiekop, J. Liebigs Ann. 1954, 587, 51.
19. Carlier, P.; Gelas-Mialhe, Y.; Vessière, R. Can. J. Chem. 1977, 55, 3190; Gaillot, J. M.; Gelas-Mialhe, Y.; Vessière, R. Can. J. Chem. 1979, 57, 1958.
20. Carlier, P.; Gelas-Mialhe, Y.; Vessière, R. Can. J .Chem. 1977, 55, 3190; Gaillot, J. M.; Gelas-Mialhe, Y.; Vessière, R. Can. J. Chem. 1979, 57, 1958.
21. Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903; Simpkins, N. S. Tetrahedron 1990, 46, 6951 and references therein.
22. Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903; Simpkins, N. S. Tetrahedron 1990, 46, 6951 and references therein.
23. Kataev, E.G.; Tantasheva, F. R.; Berdnikov, E. A.; Samitov, Y. Y. Zh. Org. Khim. 1967, 3, 1948.
24. 13C-NMR spectroscopy and by elemental analysis or high resolution mass spectrometry.
25. Yamada, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jap. 1983, 56, 949.