Cyclododecatetraene tetraepoxide: Highly diastereofacial epoxidation of all-(Z)-1,4,7,10-cyclododecatetraene and selective synthesis of bridged bis-oxocanes

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3319-3322

  Guiard, Sophie ^a   Giorgi, Michel ^a   Santelli, Maurice ^a   Parrain, Jean Luc ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SELECTIVITY; OLEFINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EPOXIDATION;

EPOXY RESINS;

1,4,7,10 CYCLODODECATETRAENE; 1,4,7,10 TETRAEPOXIDE; 3 CHLOROPERBENZOIC ACID; CYCLODODECATETRAENE TETRAEPOXIDE; DECANE; DIEPOXYOXABICYCLO[5.5.1]TRIDECANE; DIMETHYLDIOXIRANE; DODECANE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; HYDROBROMIC ACID; LEWIS ACID; OXIDE; OXOCANE DERIVATIVE; POTASSIUM BROMIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BINDING; DIASTEREOISOMER; EPOXIDATION; REACTION ANALYSIS; SOLUBILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0345381994     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026736r     Document Type: Article

References (37)

1. (a) Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001; p 1051.
2. (b) Erden, I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, UK, 1996; Vol. 1A, pp 105-117.
3. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
4. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
5. (a) Rebek, J., Jr.; Marshall, L.; McManis, J.; Wolak, R. J. Org. Chem. 1986, 51, 1649-1653.
6. (b) Koerner, T.; Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1999, 64, 196-201.
7. Adam, W.; Smerz, A. Bull. Soc. Chim. Belg. 1996, 105, 581- 599.
8. (a) Bach, R. D.; Owensby, A. L.; Gonzales, C.; Schlegel, H. B. J. Am. Chem. Soc. 1991, 113, 2338-2339.
9. (b) Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385-3386.
10. (c) Houk, K. N.; Liu, J.; DeMello, L. C.; Kondroski, K. R. J. Am. Chem. Soc. 1997, 119, 12982-12983.
11. (d) Bach, R. D.; Estévez, C. M.; Winter, J. E.; Glukhovtsev, M. N. J. Am. Chem. Soc. 1998, 120, 680-685.
12. (e) Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. Org. Chem. 1999, 64, 3858-3860.
13. (f) Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. Org. Chem. 2000, 65, 2030-2042.
14. (g) Adam, W.; Bach, R. D.; Dmitrenko, O.; Saha-Möller, C. R. J. Org. Chem. 2000, 65, 6715-6728.
15. (h) Washington, I.; Houk, K. N. Angew. Chem., Int. Ed. 2001, 40, 4485-4488.
16. Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841.
17. Fehr, C. Angew. Chem., Int. Ed. 1998, 37, 2407-2409.
18. Han, X.; Crane, S. N.; Corey, E. J. Org. Lett. 2000, 2, 3437-3438.
19. Capdevila, J. H.; Falck, J. R. Prostaglandins & Other Lipid Mediators 2000, 62, 271-292.
20. Guiard, S.; Santelli, M.; Parrain, J.-L. Synlett 2001, 553-555.
21. Krause, A.; Musso, H.; Boland, W.; Ahlrichs, R.; Gleiter, R.; Boese, R.; Bär, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1379-1980.
22. Person, G.; Keller, M.; Prinzbach, H. Liebigs Ann. Org. Bioorg. Chem. 1996, 4, 507-527 and references therein.
23. (a) Haag, R.; Zuber, R.; Donon, S.; Lee, C.-H.; Noltemeyer, M.; Johnsen, K.; de Meijere, A. J. Org. Chem. 1998, 63, 2544-2547.
24. (b) Eckrich, R.; Neumann, B.; Stammler, H.-G.; Kuck, D. J. Org. Chem. 1996, 61, 3839-3843.
25. -3.
26. -3.
27. -3.
28. (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384.
29. (b) Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765-1784.
30. (a) Alvarez, E.; Diaz, M. T.; Perez, R.; Ravelo, J.-L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martin, J. D. J. Org. Chem. 1994, 59, 2848-2876 and references therein.
31. (b) McDonald, F. E.; Wang, X.; Do, B.; Hardcastle, K. I. Org. Lett. 2000, 2, 2917-2919.
32. (c) McDonald, F. E.; Bravo, F.; Wang, X.; Wei, X.; Toganoh, M.; Rodriguez, J. R.; Do, B.; Neiwert, W. A.; Hardcastle, K. I. J. Org. Chem. 2002, 67, 2515-2523.
33. X-ray structure: 3.775 Å. B3LYP/6.31G optimized geometry: 3.363 Å.
34. -3.
35. -3.
36. Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428-2429.
37. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.