Synthesis of γ-hydroxy α,β-unsaturated amides by base induced isomerization of epoxy amides

Tetrahedron

Volumn 54, Issue 33, 1998, Pages 9613-9622

  Brooks, Peter B ^a   Marson, Charles M ^a,b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZOIC ACID DERIVATIVE; EPOXIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; EPOXIDATION; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032514521     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00519-5     Document Type: Article

References (31)

1. 1. Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; Fenical, W.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757.
2. 2. (a) Awruch, J.; Frydman, B. Tetrahedron Lett. 1976, 46, 4121;
3. (b) Frydman, R. B.; Tomaro, M. L.; Wanschelbaum, A.; Andersen, E.; Awruch, J.; Frydman, B. Biochemistry 1973, 12, 5253.
4. 3. Lightner, D. A.; Pak, C.-S. J. Org. Chem. 1975, 40, 2725.
5. 4. Hasegawa, T.; Harada, S. Jpn. Kokai Tokkyo Koho, JP 62,190,161 1987; Chem. Abstr. 1988, 109, 5279.
6. 4. Hasegawa, T.; Harada, S. Jpn. Kokai Tokkyo Koho, JP 62,190,161 1987; Chem. Abstr. 1988, 109, 5279.
7. 5. Nicolaou, K. C. Tetrahedron 1977, 33, 683.
8. 6. (a) Hanessian, S.; Sumi, K. Synthesis 1991, 1083;
9. (b) Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
10. 7. König, H.; Metzger, H. Chem. Ber. 1965, 98, 3733.
11. 8. Johnson, C. D.; Lane, S.; Edwards, P. N.; Taylor, P. J. J. Org. Chem. 1988, 53, 5130.
12. 9. Matsushita, Y.; Sugamoto, K.; Nakama, T.; Sakamoto, T.; Matsui, T. Tetrahedron Lett. 1995, 36, 1879.
13. 10. Bennani, Y. L.; Sharpless. K. B. Tetrahedron Lett. 1993, 34, 2083.
14. 11. a Rickborn, B.; Thummel, R. P. J. Org. Chem. 1969, 34, 3583;
15. b Thummel, R. P.; Rickborn, B. J. Am Chem. Soc. 1970, 92, 2064.
16. 12. a Mohr, P.; Rösslein, L.; Tamm, C; Tetrahedron Lett. 1989, 30, 2513;
17. b Cory, R. M.; Ritchie, B. M. Shrier, A. M. Tetrahedron Lett. 1990, 31, 6789.
18. 13. Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 345.
19. 14. Miginiac, P.; Zamlouty, G. Bull. Soc. Chim. Fr. 1975, 1740.
20. 15. Crandall, J. K.; Lin, L.-H. C. J. Org. Chem. 1968, 33, 2375.
21. 16. Kissel, C. L.; Rickborn, B. J. Org. Chem. 1972, 37, 2060.
22. 17. Sicher, J.; Závada J.; Pánková, M. J. Chem. Soc., Chem. Commun. 1968, 1147.
23. 18. Marson, C. M.; Grabowska, U.; Fallah, A; Walsgrove, T.; Eggleston, D. S.; Baures, P. W. J. Org. Chem. 1994, 59, 291.
24. 19. Marson, C. M.; Grabowska, U.; Walsgrove, T.; Eggleston, D. S.; Baures, P. W. J. Org. Chem. 1994, 59, 284.
25. 20. Letch, R. A.; Linstead, R. P. J. Chem. Soc. 1932, 443.
26. 21. Wallach, O. Annalen., 1907, 353, 292.
27. 22. van der Veen, R. H.; Cerfontain, H. J. Org. Chem. 1985, 50, 342.
28. 23. Cornforth, J. W.; Ross, F. P.; Wakselman, C. J. Chem. Soc, Perkin Trans. 1 1975, 429.
29. 24. Jacobsen, N; Torssell, K. Acta Chem. Scand. 1973, 27, 3211.
30. 25. Hernandez, E.; Hoberg, H. J. Organometal. Chem. 1987, 327, 429.
31. 26. Koenig, H.; Metzger, H. Chem. Ber. 1965, 98, 3733.