First example of direct RuO4- catalyzed oxidation of isoxazolidines to 3-isoxazolidones

Journal of Organic Chemistry

Volumn 72, Issue 10, 2007, Pages 3958-3960

  Piperno, Anna ^a   Chiacchio, Ugo ^b   Iannazzo, Daniela ^a   Giofrè, Salvatore V ^a   Romeo, Giovanni ^a   Romeo, Roberto ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYL ACETATE; ISOXAZOLIDINES; RUTHENIUM OXIDES;

CATALYST ACTIVITY; ESTERS; OXIDATION; REACTION KINETICS; RUTHENIUM COMPOUNDS; SUBSTITUTION REACTIONS;

NITROGEN COMPOUNDS;

3 ISOXALIDONE; ISOXAZOLIDINE DERIVATIVE; OXIDE; PERIODATE SODIUM; RUTHENIUM OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; RACEMIZATION;

ALKENES; CATALYSIS; ISOXAZOLES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RUTHENIUM COMPOUNDS; STEREOISOMERISM;

EID: 34248581890     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070211n     Document Type: Article

References (23)

1. Peisach, D.; Chipman, D. M.; Van Ophem, P.W.; Manning, J. M.; Ringe, D. J. Am. Chem. Soc. 1998, 120, 2268.
2. Rosenthal, G. A. Plant Physiol. 1990, 94, 1.
3. Grunwald, C.; Rundfeldt, C.; Lankau, H. J.; Arnold, T; Höfgen, N.; Dost, R.; Egerland, U.; Hofmann, H. J.; Unverferth, K. J. Med. Chem. 2006, 49, 1855.
4. De Amici, M.; De Micheli, C.; Grana, E.; Rodi, R.; Zonta, F.; Santagostino-Barbone, M. G. Eur. J. Med. Chem. 1989, 24, 171.
5. (a) Conti, P.; Dallanoce, C.; De Amici, M.; De Micheli, C.; Ebert, B. Bioorg. Med. Chem. Lett. 1997, 7, 1033.
6. (b) Dallanoce, C.; Conti, P.; De Amici, M.; De Micheli, Barocelli, E.; Chiavarini, M.; Ballabeni, V.; Bertoni, S.; Impicciatore, M. Bioorg. Med. Chem. 1999, 7, 1539.
7. (a) Krogsgaard-Larsen, P.; Nielsen, L.; Falch, E.; Curtis, D. R.; Lodge, D.; Johnston, G. A. J. Neurochem. 1979, 32, 1717.
8. (b) Krogsgaard-Larsen, P.; Nielsen, L.; Falch, E.; Curtis, D. R. J. Med. Chem. 1985, 28, 1612.
9. Caldirola, P.; De Amici, M.; De Micheli, C. Tetrahedron Lett. 1986, 27, 4651.
10. De Amici, M.; Magri, P.; De Micheli, C.; Cateni, F.; Bovara, R.; Carrea, G.; Riva, S.; Casalone, G. J. Org. Chem. 1992, 57, 2825.
11. Carrea, G.; De Amici, M.; De Micheli, C.; Liverani, P.; Carnielli, M.; Riva, S. Tetrahedron: Asymmetry 1993, 4, 1063.
12. (a) Plietker, B. Synthesis 2005, 15, 2453.
13. (b) Kaname, M.; Yoshifuji, S. Tetrahedron Lett. 1992, 33, 8103.
14. (c) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1617.
15. (a) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335.
16. (b) Merino, P.; Revuelta, J.; Tejero, T.; Chiacchio, U.; Rescifina, A.; Piperno, A.; Romeo, G. Tetrahedron: Asymmetry 2002, 13, 167.
17. (a) Li, P.; Gi, H. J.; Sun, L.; Zhao, K. J. Org. Chem. 1998, 63, 366.
18. (b) Mzengeza S.; Whitney, R. A. J. Org. Chem. 1988, 53, 4074.
19. Chiacchio, U.; Romeo, G.; Uccella, N. Trends Heterocycl. Chem. 1995, 4, 261.
20. (a) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
21. (b) Plietker, B. Synthesis 2005, 15, 2453.
22. Mzenga, S.; Whitney, A. R. J. Chem. Soc., Chem. Commun. 1984, 606.
23. Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 321.