Synthesis of β-lactams from a N-rhenaimine: Effect of the transition metal on the energetic profile of the Staudinger reaction

Journal of the American Chemical Society

Volumn 125, Issue 13, 2003, Pages 3706-3707

  Hevia, Eva ^a   Pérez, Julio ^a   Riera, Víctor ^a   Miguel, Daniel ^b   Campomanes, Pablo ^a   Menéndez, M Isabel ^a   Sordo, Tomás L ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; PYRIDINE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CRYSTALLIZATION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENERGY TRANSFER; SOLID STATE; STAUDINGER REACTION; STOICHIOMETRY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

ANTI-BACTERIAL AGENTS; BETA-LACTAMS; CYCLIZATION; ETHYLENES; KETONES; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; RHENIUM; THERMODYNAMICS;

EID: 0242668803     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034070s     Document Type: Article

References (18)

1. (a) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982: Vol. 1-3.
2. (b) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1997.
3. (a) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Román, P.; Luque, A.; Martinez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360.
4. (b) Birchler, A. G.; Liu, F.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 7737.
5. (c) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, J.; Marshall, G. R.; Almqvist, F. Org. Lett. 2000, 2, 2065.
6. (a) Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995.
7. (b) López, R.; Sordo, T. L.; Sordo, J. A.; González, J. J. J. Org. Chem. 1993, 58, 7036.
8. (c) López, R.; Ruiz-López, M. F.; Rinaldi, D.; Sordo, J. A.; Sordo, T. J. J. Phys. Chem. 1996, 100, 10600.
9. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626.
10. Hevia, E.; Pérez, J.; Riera, V.; Miguel, D. Angew. Chem., Int. Ed. 2002, 41, 3858.
11. Hevia, E.; Pérez, J.; Riera, V.; Miguel, D. Chem. Commun. 2002, 1814.
12. See for instance: Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
13. Hegedus, L. S.; Week, G. de: D'Andrea, S. J. Am. Chem. Soc. 1988, 110, 2122.
14. Piotti, M. E.; Alper, H. J. Am. Chem. Soc. 1996, 118, 111.
15. Birkofer, L.; Schramm, J. Justus Liebigs Ann. Chem. 1977, 760.
16. Panunzio, M.; Zarantonello, P. Org. Process Res. Dev. 1998, 2, 49.
17. Martelli, G.; Spunta, G.; Panunzio, M. Tetrahedron Lett. 1998, 39, 6257.
18. Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249.