Trans -diastereoselective synthesis of 3-phthalimido β-lactams via a two step-Staudinger reaction

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4409-4412

  Bandini, Elisa ^a   Martelli, Giorgio ^a   Spunta, Giuseppe ^a   Bongini, Alessandro ^a   Panunzio, Mauro ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; BETA LACTAM DERIVATIVE; IMINE; PHTHALIMIDE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; TRANS ISOMER;

EID: 0030009969     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00841-6     Document Type: Article

References (25)

1. Bonanomi, G.; Donati, D.; Perboni, A.; Camerini, C.; Panunzio, M. Tetrahedron Lett. 1996,37, 2467.
2. Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron 1996, 52, 1685-1698.
3. Cainelli, G.; Panunzio, M. Farmaco 1991, 46, 177-190.
4. Cainelli, G.; Panunzio, M.; Giacomini, D.; Bandini, E.; Martelli, G.; Spunta, G. In NATO-Asi; 1996 In Press.
5. Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G.; Da Col, M. Tetrahedron 1995, 51, 5067.
6. Andreoli, P.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. J. Org. Chem. 1991, 56, 5984-5990.
7. Andreoli, P.; Billi, L.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron 1991, 47, 9061
8. Bandini, E.; Cainelli, G.; Giacomini, D.; Martelli, G.; Panunzio, M.; Spunta, G. Biorganic and Medicinal Chem. Lett. 1993, 3, 2347 and Ref. therein cited.
9. Bandini, E.; Cainelli, G.; Giacomini, D.; Martelli, G.; Panunzio, M.; Spunta, G. Gazz. Chim. It. 1993, 123, 509.
10. Panunzio, M.; Giacomini, D.; Bandini, E. In Seminars in Organic Synthesis; S.C.I., Ed.; 1993; Vol. XVIII; pp 47-69.
11. Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; G. Georg, Ed.; VCH: New York, 1993; pp 318
12. Koppel, G. A. Small Ring Heterocycles; Wiley: New York, 1983; Vol. 42, pp 219-441.
13. Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustand, D. C. J. Am. Chem. Soc. 1991, 113, 5784.
14. Cooper, R. D. G.; Daugherty, B. W.; Boyd, D. B. Pure App. Chem. 1987,59,485-492.
15. Brady, W. T.; Gu, Y. Q. J. Org. Chem. 1989, 54, 2838.
16. Birkofer, L.; Schramm, J. Liebigs Ann. Chem. 1977, 760-766.
17. Paul, L.; Draeger, A.; Hilgetag, G. Chem. Ber. 1966, 99, 1957.
18. Paul, L.; Zieloff, K. Chem. Ber. 1966, 99, 1431.
19. Ghosez, L. Pure & App. Chem. 1996, 68, 15-22.
20. Ghosez, L.; Bayard, P.; Nshimyumukiza, P.; Gouverneur, V.; Sainte, F.; Beaudegnies, R.; Rivera, M.; Frisque-Hesbain, A. M.; Wynants, C. Tetrahedron 1995, 51, 11021.
21. All the spectral data of the products obtained are consistent with the structures reported
22. Pacansky, J.; Chang, J. S.; Prown, D., W,; Schwarz, W. J. J. Org. Chem. 1982, 47, 2233.
23. Cooper, R. D., G,; Daugherty, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485.
24. Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085-2093.
25. Stewart, J. J. P. MOPAC 6.0-Q.C.P.E. 455 Indiana University, Indiana: Bloomington.