The azomethine ylide strategy for β-lactam synthesis. Azapenams and 1-azacephams

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 17, 2002, Pages 2014-2021

  Brown, David ^a   Brown, Giles A ^a   Andrews, Mark ^a   Large, Jonathan M ^a   Urban, Dominique ^a   Butts, Craig P ^a   Hales, Neil J ^b   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; CRYSTALLINE MATERIALS; HEATING; KETONES; NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SOLUTIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION ANALYSIS;

CYCLOADDITION REACTIONS;

AROMATIC COMPOUNDS;

EID: 0036025621     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b203890k     Document Type: Article

References (58)

1. S.R. Martel, D. Planchenault, R. Wisedale, T. Gallagher, N.J. Hales Chem. Commun. 1997, 1897.
2. D. Brown, G.A. Brown, S.R. Martel, D. Planchenault, E. Turmes, K.E. Walsh, R. Wisedale, N.J. Hales, C.W.G. Fishwick, T. Gallagher J. Chem. Soc., Perkin Trans. 1 2000, 1270.
3. T. Gallagher J. Heterocycl. Chem. 1999, 36, 1365.
4. S.R. Martel, R. Wisedale, T. Gallagher, L.D. Hall, M.F. Mahon, R.H. Bradbury, N.J. Hales J. Am. Chem. Soc. 1997, 119, 2309.
5. D. Planchenault, R. Wisedale, T. Gallagher, N.J. Hales J. Org. Chem. 1997, 62, 3438.
6. M.D. Andrews, G.A. Brown, J.P.H. Charmant, T.M. Peakman, A. Rebello, K.E. Walsh, T. Gallagher, N.J. Hales Chem. Commun. 1999, 249.
7. G.A. Brown, K.M. Anderson, M. Murray, T. Gallagher, N.J. Hales Tetrahedron 2000, 56, 5579.
8. G.A. Brown, K.M. Anderson, J.M. Large, D. Planchenault, D. Urban, N.J. Hales, T. Gallagher J. Chem. Soc., Perkin Trans. 1 2001, 1897.
9. G. Johnson, B.C. Ross J. Chem. Soc., Chem. Commun. 1981, 1269.
10. G. Johnson, P.M. Rees, B.C. Ross J. Chem. Soc., Chem. Commun. 1984, 970.
11. T. Shibata, Y. Sugimura, S. Sato, K. Kawazoe Heterocycles 1985, 23, 3069.
12. M. Es-Sayed, T. Heiner, A. de Meijere Synlett 1993, 57.
13. Y. Hsiao, L.S. Hegedus J. Org. Chem. 1997, 62, 3586.
14. E. Kuester, L.S. Hegedus Organometallics 1999, 18, 5318.
15. S. Wolfe, J.B. Ducep, G. Kannengiesser, W.S. Lee Can. J. Chem. 1972, 50, 2902.
16. A.K. Bose, J.C. Kapur, J.L. Fahey, M.S. Manhas J. Org. Chem. 1973, 38, 3437.
17. D. Davies, M.J. Pearson J. Chem. Soc., Perkin Trans. 1 1981, 2539.
18. M.J. Pearson J. Chem. Soc., Perkin Trans. 1 1981, 2544.
19. S.D. Sharma, U. Mehra Tetrahedron Lett. 1984, 25, 1849.
20. S.D. Sharma, S.K. Arora, U. Mehra Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24, 895.
21. S.D. Sharma, U. Mehra, V. Kaur Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1986, 25, 1061.
22. H.H. Wasserman, M.D. Xia, A.J. Carr, W.T. Han, M.G. Siegel Tetrahedron 2000, 56, 5621.
23. J.-P. Anselme, in The chemistry of the carbon–nitrogen double bond, ed. S Patai, Interscience, London, 1970, ch. 7, p. 299.
24. G. Tennant, Comprehensive Organic Chemistry, ed. I. O. Sutherland, Pergamon Press, Oxford, 1979, vol. 2, p. 385.
25. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, eds. J. E. Baldwin and P. D. Magnus, Pergamon Press, Oxford, 1990.
26. T.T. Howarth and I. Stirling, Ger. Offen. 2,655,675.
27. T.T. Howarth and I. Stirling Chem. Abstr., 1977, 87, 102313.
28. A.G. Brown, D.F. Corbett, J. Goodacre, J.B. Harbridge, T.T. Howarth, R.J. Ponsford, I. Stirling, T.J. King J. Chem. Soc., Perkin Trans. 1 1984, 635.
29. A.M. Kanazawa, J.-N. Denis, A.E. Greene J. Org. Chem. 1994, 59, 1238.
30. W.B. Jennings, C.J. Lovely Tetrahedron Lett. 1988, 29, 3725.
31. A.G. Brown, D.F. Corbett, T.T. Howarth J. Chem. Soc., Chem. Commun. 1977, 359.
32. S.M. Schmitt, D.B.R. Johnston, B.G. Christensen J. Org. Chem. 1980, 45, 1135.
33. R. Sharva, R.J. Stoodley, A. Whiting J. Chem. Soc., Perkin Trans. 1 1987, 2361.
34. W. Maison, M. Kosten, A. Charpy, J. Kintscher-Langenhagen, I. Schlemminger, A. Lutzen, O. Westerhoff, J. Martens Eur. J. Org. Chem. 1999, 2433.
35. F.W. Fowler Adv. Heterocycl. Chem. 1971, 13, 45.
36. Z. Bende, I. Bitter, L. Toke, L. Weber, G. Toth, F. Janke Liebigs Ann. Chem. 1982, 2146.
37. D.M.B. Hickey, C.J. Moody, C.W. Rees J. Chem. Soc., Perkin Trans. 1 1986, 1119.
38. O. Meth-Cohn, N.J.R. Williams, A. MacKinnon, J.A.K. Howard Tetrahedron 1998, 54, 9837.
39. D. Knittel Synthesis 1985, 186.
40. M.J. Alves, T.L. Gilchrist J. Chem. Soc., Perkin Trans. 1 1998, 299.
41. M.J. Alves, T.L. Gilchrist Tetrahedron Lett. 1998, 39, 7579.
42. A. Laurent, P. Mison, A. Nafti, N. Pellissier Tetrahedron 1979, 35, 2285.
43. A. Padwa, Y. Kulkarni Tetrahedron Lett. 1979, 107.
44. M.J. Alves, T.L. Gilchrist, J.H. Sousa J. Chem. Soc., Perkin Trans. 1 1999, 1305.
45. E.J. Corey, R.D. Balanson Heterocycles 1976, 5, 445.
46. K. Sha, S.L. Ouyang, D.Y. Hsieh, R.C. Chang, S.C. Chang J. Org. Chem. 1986, 51, 1490.
47. D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, D.M. Barnes J. Am. Chem. Soc. 1993, 115, 5328.
48. Y.H. Lim, W.K. Lee Tetrahedron Lett. 1995, 36, 8431.
49. G.A. Molander, P.J. Stengel J. Org. Chem. 1995, 60, 6660.
50. G.A. Molander, P.J. Stengel Tetrahedron 1997, 53, 8887.
51. T. Honda, F. Ishikawa Chem. Commun. 1999, 1065.
52. P.H. Crackett, C.M. Pant, R.J. Stoodley J. Chem. Soc., Perkin Trans. 1 1984, 2785.
53. M.D. Bachi, R. Breiman, H. Meshulam J. Org. Chem. 1983, 48, 1439.
54. A.G. Hortmann, D.A. Robertson, B.K. Gillard J. Org. Chem. 1972, 37, 322.
55. V.N. Belov, M.A. Kuznetsov Zh. Org. Khim. 1988, 24, 1288 Chem. Abstr. 1989, 110, 75232a.
56. R. Muller, R. Gust, U. Klement, H. Schonenberger Chem. Ber. 1991, 124, 2381.
57. J. Legters, L. Thijs, B. Zwanenburg Recl. Trav. Chim. Pays-Bas 1992, 111, 16.
58. S. Chandrasekhar, M. Ahmed Tetrahedron Lett. 1999, 40, 9325.