A mild, catalytic, and highly selective method for the oxidation of α,β-enones to 1,4-enediones

Journal of the American Chemical Society

Volumn 125, Issue 11, 2003, Pages 3232-3233

  Yu, Jin Quan ^a   Corey, E J ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 ENEDIONE DERIVATIVE; ALPHA,BETA ENONE DERIVATIVE; NATURAL PRODUCT; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; EVAPORATION; OXIDATION; REACTION ANALYSIS; REDUCTION; ROOM TEMPERATURE; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ALKENES; CATALYSIS; HYDROXIDES; KETONES; OXIDATION-REDUCTION; PALLADIUM; TERT-BUTYLHYDROPEROXIDE;

EID: 0037454309     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0340735     Document Type: Article

References (32)

1. Salvá, J.; Faulkner, D. J. J. Org. Chem. 1990, 55, 1941.
2. (a) Nerali, S. B.; Chakravarti, K. K. Sci. Cult. (India) 1969, 35, 110.
3. (b) Bollinger, P.; Zardin-Tartaglia, T. Helv. Chim. Acta 1976, 59, 1809.
4. (c) Chexal, K. K.; Tamm, C.; Clardy, J. Helv. Chim. Acta 1979, 62, 1129.
5. Fieser, L. F.; Fieser, M. Steroids; Reinhold Publishing Corp.: New York, NY, 1959.
6. Webb, J. S.; Cosulich, D. B.; Mowat, J. H.; Patrick, J. B.; Broschard, R. W.; Meyer, W. E.; Williams, R. P.; Wolf. C. F., Fulmor, W.; Pidacs, C.; Lancaster, J. E. J. Am. Chem. Soc. 1962, 84, 3185.
7. Seto, H.; Cary, L. W.; Tanabe, M. J. Chem. Soc., Chem. Commun. 1973, 867.
8. Ballini, R.; Astolfi, P. Liebigs Ann. 1996, 1879.
9. Danishefsky, S.; Kahn, M. Tetrahedron Lett. 1981, 22, 489.
10. Ballini, R.; Bosica, G. Tetrahedron 1995, 51, 4213.
11. (a) Pearlman, W. M. Tetrahedron Lett. 1967, 1663.
12. (b) Handbook of Reagents for Organic Synthesis. Oxidizing and Reducing Agents: Burke, S. D., Danheiser, R. L., Eds.; J. Wiley: New York, 1999; p 285.
13. (a) for 2-cyclopenten-1,4-dione: De Puy, C. H.; Zaweski, E. F. J. Am. Chem. Soc. 1959, 81, 4920.
14. (b) For 2-cyclohexen-1,4-dione: Hung, S.-C.; Liao, C.-C. Tetrahedron Lett. 1991, 32, 4011.
15. 2-on-C should be added.
16. 2 gas; on a larger scale, this should be vented from the reactor.
17. 2-on-carbon is prereduced to Pd(0)-on-carbon by stirring with hydrogen, it does not serve as an effective reaction catalyst, although it is gradually oxidized by t-BuOOH to a form that shows some catalytic activity.
18. (a) D'Auria, M.; De Mico, A.; D'Onofrio, F.; Scettri, A. Synthesis 1985, 988.
19. (b) Rosenthal, D.; Grabowich, P.; Sabo, E. F.; Fried, J. J. Am. Chem. Soc. 1963, 85, 3971.
20. Jasiczak, J. J. Chem. Soc., Perkin Trans. 1 1988, 2687.
21. (a) Corey, E. J.; Crouse, D. J. Org. Chem. 1968, 33, 298.
22. (b) Echavarren, A. M.; Pérez, M.; Castaño, M.; Cuerva, J. M. J. Org. Chem. 1994, 59, 4179.
23. (c) Bonete, P.; Nájera, C. Tetrahedron 1995, 51, 2763.
24. (d) Ballini, R.; Bosica, G. J. Org. Chem. 1994, 59, 5466.
25. (e) Kulkowit, S.; McKervey, M. A. J. Chem. Soc., Chem. Commun. 1978, 1069.
26. Yu, J.-Q.; Corey, E. J. Org. Lett. 2002, 4, 2727.
27. (a) Bartlett, P. D.; Günther, P. J. Am. Chem. Soc. 1966, 88, 3288.
28. (b) Barlett, P. D.; Guaraldi, G. J. Am. Chem. Soc. 1967, 89, 4799.
29. For the oxidative formation of peroxy radicals from hydroperoxides, see: (a) Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc., Chem. Commun. 1990, 1102. (b) Kharasch, M. S.; Pauson, P.; Nudenberg, W. J. Org. Chem. 1953, 18, 323. (c) Araneo, S.; Fontana, F.; Minisci, F.; Recupero, F.; Serri, A. J. Chem. Soc., Chem. Commun. 1995, 1399.
30. For the oxidative formation of peroxy radicals from hydroperoxides, see: (a) Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc., Chem. Commun. 1990, 1102. (b) Kharasch, M. S.; Pauson, P.; Nudenberg, W. J. Org. Chem. 1953, 18, 323. (c) Araneo, S.; Fontana, F.; Minisci, F.; Recupero, F.; Serri, A. J. Chem. Soc., Chem. Commun. 1995, 1399
31. For the oxidative formation of peroxy radicals from hydroperoxides, see: (a) Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc., Chem. Commun. 1990, 1102. (b) Kharasch, M. S.; Pauson, P.; Nudenberg, W. J. Org. Chem. 1953, 18, 323. (c) Araneo, S.; Fontana, F.; Minisci, F.; Recupero, F.; Serri, A. J. Chem. Soc., Chem. Commun. 1995, 1399
32. For radical catalyzed carbonyl-forming elimination, see: Courmeidge, J. L.; Bush, M.; Loh, L. S. Tetrahedron 1992, 48, 3835.