Synthetic routes to β-lactams. Some unexpected hydrogen atom transfer reactions

Tetrahedron

Volumn 54, Issue 10, 1998, Pages 2087-2098

  Boiteau, Laurent ^b   Boivin, Jean ^b   Quiclet Sire, Béatrice ^a   Saunier, Jean Baptiste ^a   Zard, Samir Z ^a,b  

^a CNRS   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; BETA LACTAM; HYDROGEN; XANTHIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL;

EID: 0032485358     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10417-3     Document Type: Article

References (31)

1. 1. For recent reviews and monographs, see: (a)The Chemistry of β-Lactams , Page M. I., Ed.; Chapman & Hall: London, 1992.
2. (b) Recent Progress in Chemical Synthesis of Antibiotics , Lukacs, G.; Ohno, M.; Springer-Verlag: Berlin, 1990.
3. (c) An issue of BioMed. Chem. Lett. was recently devoted to recent advances in the chemistry and biology of β-lactams and β-lactam antibiotics : BioMed. Chem. Lett. 1993, 3, 2139-2486.
4. 2. For examples, see : (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27,1755-1822.
5. (b) Palomo, C; Aizpurua, J. M.; Ganboa, I; Carreaux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123-3130.
6. (c) Bose, A. K.; Mathur, C.; Wagle, D. R.; Naqvi, R.; Manhas, M. S.; Urbanczyk-Lipkowska, Z. Heterocycles 1994, 39, 491-496.
7. (d) Saragovi, H. U.; Fitzpatrick, D.; Raktabutr, A.; Nakanishi, H.; Kahn, M.; Greene, M. I. Science 1996, 253, 792-795.
8. (e) Ojima, I. Acc.Chem. Res. 1995, 28, 383-389.
9. (f) Ojima, I.; Kuduk, S. D.; Slater, J. C.; Gimi, R. H.; Sun, C. M. Tetrahedron 1996, 52, 209-224.
10. 3. (a) Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1991, 32, 259-262.
11. (b) Bryon Gill, G.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans 1 1994, 369-378.
12. (c) Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans 1 1994, 379-385.
13. (d) Fremont, S. L.; Belletire, J. L.; Ho, D. M. Tetrahedron Lett. 1991, 32, 2335-2338.
14. (e) Ishibashi, H.; Nakamura, N.; Sato, T.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728.
15. (f) Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans 1 1992, 2399-2407.
16. (g) Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, R.; Kodama, K.; Sato, T.; Ikeda, M. Synlett 1993, 649-650.
17. (h) T. Sato, T.; Chono, N.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans 1 1995, 1115-1120.
18. 4. Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 1397-1400.
19. 5. For a review of this work, see: Zard, S. Z. Angew. Chem. Int. Ed. Engl. 1997, 36, 672-685.
20. 6. M. D. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett., 1987, 28, 2637-2640.
21. 7. Beckwith, A. L. J.; Ingold, K. U. in Rearrangements in Ground and Excited States, de Mayo, P., Ed. Academic Press: New york, 1980, Vol.1, pp 161-310. In a recent theoretical study, the energy of activation for a 1,2; 1,3; 1,4; and 1,5 hydrogen migration has been calculated to be 41.1; 41.6; 24.6; and 17.2 KCal / Mole respectively: Viscolz; B.; Lendvay; G.; Körtvélyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
22. 7. Beckwith, A. L. J.; Ingold, K. U. in Rearrangements in Ground and Excited States, de Mayo, P., Ed. Academic Press: New york, 1980, Vol.1, pp 161-310. In a recent theoretical study, the energy of activation for a 1,2; 1,3; 1,4; and 1,5 hydrogen migration has been calculated to be 41.1; 41.6; 24.6; and 17.2 KCal / Mole respectively: Viscolz; B.; Lendvay; G.; Körtvélyesi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
23. 8. (a) Bruton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803-6811.
24. (b) Winkler, J. D.; Sridar, V.; Rubo, L.; Hey, J. P.; Haddad, N.J. Org. Chem. 1989, 54, 3004-3006.
25. (c) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605-615.
26. (d) Montevecchi, P. C. Tetrahedron Lett., 1996, 37, 6583-6586.
27. 9. See for example: (a) Bennett, S. M.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1986, 878-880.
28. (b) Winkler, J. D.; Gretler, E. A.; Williard, P. G. J. Org. Chem., 1993, 58, 1973-1975.
29. 10. Cekovic, Z.; Saicic, R. N. Tetrahedron Lett. 1990, 31, 6085-6088.
30. 11. Hahn, R. C.; Jones, G. W. J. Am. Chem. Soc. 1971, 93, 4232-4236.
31. 12. Bateson, J. H.; Baxter, A. J. G.; Roberts, P. M.; Smale, T. C.; Southgate, R. J. Chem. Soc., Perkin Trans, 1 1981, 3242-3249.