An amidyl radical cyclisation approach towards the synthesis of β-lactams

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1265-1268

  Clark, Andrew J ^a   Peacock, Joanne L ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032485220     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10772-9     Document Type: Article

References (19)

1. 1. a) Fossey, J.; Lefort, D.; Sorba, J.; Free Radicals in Organic Synthesis Wiley, Chichester, 1995
2. b) Curran, D. P. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds.; Pergamon Press, Oxford, 1991, Vol. 4, p716, and 779.
3. c) Curran, D. P. Synthesis 1988, 417 and 489,
4. d) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986.
5. 2. a) Esker, J. L.; Newcomb, M.; Advances in Heterocyclic Chemistry, 58, 1993, 1.
6. b) Zard, S. Z.; Synlett, 1996, 1148.
7. 3. Esker, J. L.; Newcomb, M.; Tetrahedron Letts., 1993, 34, 6875
8. 4. Boivin, J.; Callier-Dublanchet, A-C.; Quiclet-Sine, B.; Schiano, A. M.; Zard, S. Z.; Tetrahedron, 1995, 51, 6517.
9. 5. a) Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M.; Synlett, 1995, 912.
10. b) Ishibashi, H.; Kodama, K.; Kameoka, C.; Iriyama, H.; Sato, T.; Ikeda, M.; J. Org. Chem., 1995, 60, 1276.
11. c) Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M.; Synlett 1994, 445.
12. d) Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, R.; C.; Kodama, K.; Sato, T.; Ikeda, M.; Synlett, 1993, 649.
13. 6. a) Gill, G. B.; Pattenden, G.; Reynolds, S. J.; J. Chem. Soc., Chem. Commun., 1994, 369.
14. b) Pattenden, G.; Reynolds, S. J.; J. Chem. Soc., Chem. Commun., 1994, 379.
15. c) Pattenden, G.; Reynolds, S. J.; Tetrahedron Letts., 1991, 259.
16. 7. Psiorz, M.; Zinner, G., Synthesis, 1984, 217.
17. 8. All new compounds gave satisfactory spectroscopic details. Spectroscopic details for (4a) were identical to those reported. Sato, T.; Chono, N.; Ishibashi, H.; Ikeda, M.; J. Chem. Soc. Perkin Trans. 1; 1995, 1115.
18. 3) 4.60 (1H, d, J = 15.0Hz, NCHHPh), 3.95 (1H, d, J = 15.0Hz, NCHHPh), 3.66 (1H, m, H-4), 2.93 (1H, dd, J = 14.6, 4.9Hz, H-3), 2.91 (1H, dd, J = 13.7, 5.7Hz, CHHPh), 2.71 (1H, dd, J = 13.7, 7.6Hz, CHHPh), 2.64 (1H, dd, J = 14.6, 2.4Hz, H-3).
19. 10.Endo, Y.; Uchida, T.; Hizatate, T., Shudok, S.; Synthesis, 1994, 1096.