Tandem Ireland-Claisen rearrangement ring-closing alkene metathesis in the construction of bicyclic β-lactam carboxylic esters

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3716-3721

  Barrett, Anthony G M ^a   Ahmed, Mahmood ^a   Baker, Simon P ^a   Baugh, Simon P D ^a   Braddock, D Christopher ^a   Procopiou, Panayiotis A ^b   White, Andrew J P ^a   Williams, David J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BETA LACTAM; CARBOXYLIC ACID DERIVATIVE; ESTER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ALKENES; BETA-LACTAMS; CARBOXYLIC ACIDS; CHEMISTRY, ORGANIC; ESTERS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE;

EID: 0034674463     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991932s     Document Type: Article

References (28)

1. Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; Dimare, M.; O'Reagan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
2. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
3. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
4. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
5. Chang, S.; Grubbs, R. H. J. Org. Chem. 1998, 63, 864-866.
6. Peters, J. U.; Blechert, S. Chem. Commun. 1997, 1983-1984.
7. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130.
8. Fürstner, A.; Müller, T. Synlett 1997, 1010-1012.
9. Morehead, A.; Grubbs, R. Chem. Commun. 1998, 275-276.
10. Ahmed, M.; Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A.; Salter, M. M. Tetrahedron 1999, 55, 3219-3232.
11. Barrett, A. G. M.; Baugh, S. P. D.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A. Chem. Commun. 1997, 155-156.
12. Barrett, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1998, 63, 7893-7907.
13. Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650-657.
14. Picoul, W.; Urchegui, R.; Haudrechy, A.; Langlois, Y. Tetrahedron Lett. 1999, 40, 4797-4800.
15. Burke, S. D.; Ng, R. A.; Morrison, J. A.; Alberti, M. J. J. Org. Chem. 1998, 63, 3160-3161.
16. Miller, J. F.; Termin, A.; Koch, K.; Piscopio, A. D. J. Org. Chem. 1998, 63, 3158-3159.
17. Baldwin, J. E.; Bradley, M.; Turner, N. J.; Adlington, R. M.; Pitt, A. R.; Sheridan, H. Tetrahedron 1991, 47, 8203-8222.
18. Armstrong, A.; Brackenridge, I.; Jackson, R. F. W.; Kirk, J. M. Tetrahedron Lett. 1988, 29, 2483-2486.
19. Barrett, A. G. M.; Head, J.; Smith, M. L.; Stock, N. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1999, 64, 6005-6018.
20. Torii, S.; Tanaka, H.; Taniguchi, M.; Kameyama, Y.; Sasaoka, M.; Shiroi, T.; Kikuchi, R.; Kawahara, I.; Shimabayashi, A.; Nagao, S. J. Org. Chem. 1991, 56, 3633-3637.
21. Hauser, F. M.; Ellenberger, S. R. Synthesis 1987, 324.
22. Bateson, J. H.; Baxter, A. J. G.; Roberts, P. M.; Smale, T. C.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1981, 3242-3249.
23. Basak, A.; Khamrai, U. Synth. Commun. 1994, 24, 131-135.
24. Campbell, M. M.; Connarty, B. P. Heterocycles 1982, 19, 1853-1854.
25. Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098-3103. During these investigations, an excellent alternative method was disclosed: Kang, S. K.; Baik, T. G.; Jiao, X. H.; Lee, K. J.; Lee, C. H. Synlett 1999, 447-449.
26. Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098-3103. During these investigations, an excellent alternative method was disclosed: Kang, S. K.; Baik, T. G.; Jiao, X. H.; Lee, K. J.; Lee, C. H. Synlett 1999, 447-449.
27. Clarke, H. T. J. Chem. Soc. 1910, 97, 416-429.
28. During these investigations an alternative esterification procedure was disclosed and employed, with comparable results: Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342-2347.