Synthesis of (E)-α,β-unsaturated esters with total or high diastereoselectivity from α,β-epoxyesters

Organic Letters

Volumn 4, Issue 2, 2002, Pages 189-191

  Concellón, José M ^a   Bardales, Eva ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001114037     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016894p     Document Type: Article

References (29)

1. In the best of our knowledge, the scarce papers published contain only one example of this transformation, and only the synthesis of (E)-ethyl cinnamate from the corresponding α,β-epoxyester has been described in high yield and with total diastereoselection: Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468-4475.
2. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
3. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
4. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
5. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
6. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
7. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
8. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
9. 2: (c) Emmer, G.; Graf, W. Helv. Chim. Acta 1981, 64, 1398-1406. (d) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070. (e) Ekong, D. E. U.; Olagbemi, E. O. J. Chem. Soc. C 1966, 944-946. (f) Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1983, 1107-1108. (g) Banerji, J.; Chatterjee, A.; Ghoshal, N.; Das, A.; Sarkar, S. J. Indian Chem. Soc. 1982, 59, 145-149. (h) Bennett, R. D.; Hasegawa, S. Phytochemistry 1982, 21, 2349-2354.
10. (a) Ameer, F.; Drewes, S. E.; Hoole, R.; Kaye, P. T.; Pitchford, A. T. J. Chem. Soc., Perkin Trans. 1 1985, 2713-2717.
11. (b) Kobayashi, T.; Nitta, M. Chem. Lett. 1982, 325-328.
12. (c) Vedejs, E.; Fuchs, P. L. J. Am. Chem. Soc. 1973, 95, 822-825.
13. (a) Rosenblum, M.; Saldi, M. R.; Madhavarao, M. Tetrahedron Lett. 1975, 16, 4009-4011.
14. (b) Bissing, D. E.; Speziale, A. J. J. Am. Chem. Soc. 1965, 87, 2683-2690.
15. Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257-11270.
16. (a) Frazier, J. W.; Staszak, M. A.; Weigel, L. O. Tetrahedron Lett. 1992, 33, 857-860.
17. (b) Alper, H.; Des Roches, D. Tetrahedron Lett. 1977, 18, 4155-4158.
18. (a) Meth-Cohn, O.; Moore, C.; Taljaard, H. T. J. Chem. Soc., Perkin Trans. 1 1988, 2663-2674.
19. (b) Kehrli, A. R. H.; Taylor, D. A. H. J. Chem. Soc., Perkin Trans, 1 1990, 2067-2070.
20. Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. Angew. Chem., Int. Ed. 1999, 38, 2384-2386.
21. Concellón, J. M.; Pérez-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775.
22. Concellón, J. M.; Pérez-Andrés, J. A.; Rodríguez-Solla, H. Chem. Eur. J. 2001, 7, 3062-3068.
23. Concellón, J. M.; Bernad, P. L.; Bardales, E. Org. Lett. 2001, 3, 937-939.
24. 2 (1.6 mmol) in THF (19 mL) was added, under nitrogen atmosphere, dropwise to a stirred solution of the corresponding epoxyester 1 (0.4 mmol) in THF (4 mL) at room temperature or at reflux. The reaction mixture was stirred for 90 min (rt) or 2 h (reflux), and then the reaction was quenched with aqueous HCl (20 mL of a 0.1 M solution). Usual workup afforded crude α,β-unsaturated ester 2, which was purified by column flash chromatography over silica gel (10:1 hexane/ethyl acetate).
25. By example, the diastereoselectivity of the Wittig reaction, to obtain αl,β-unsaturated esters, decreases with bulky alcoholic groups: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
26. To the best of our knowledge, no diastereoselective synthesis of tetrasubstituted α,β-unsaturated esters from α,β-epoxiesters has been described.
27. 1H NMR determination was in agreement with the de obtained by GC-MS.
28. Similar six-membered ring transition state models have been proposed to explain the selectivity in other reactions of Smh: (a) Urban, D.; Skrydstrup, T.; Beau, J. M. J. Org. Chem. 1998, 63, 2507-2516. (b) Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 709, 453-463.
29. Similar six-membered ring transition state models have been proposed to explain the selectivity in other reactions of Smh: (a) Urban, D.; Skrydstrup, T.; Beau, J. M. J. Org. Chem. 1998, 63, 2507-2516. (b) Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 709, 453-463.