Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 17. Preparation of aliphatic amino acid derived γ-alkoxycarbonylamino-β-oxo ylides and pyrolysis to give α,β-acetylenic γ-amino acid and GABA analogues

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 4, 2002, Pages 533-541

  Aitken, R Alan ^a   Karodia, Nazira ^a   Massil, Tracy ^a   Young, Robert J ^b  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CHEMICAL BONDS; CONDENSATION; ESTERS; EXTRUSION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; PHOSPHORUS COMPOUNDS; PYROLYSIS; SYNTHESIS (CHEMICAL); VACUUM APPLICATIONS;

TRIPLE BONDS;

AMINO ACIDS;

EID: 0036008099     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b110243e     Document Type: Article

References (33)

1. R. A. Aitken, M.J. Drysdale, L. Hill, K.W. Lumbard, J.R. MacCallum, S. Seth Tetrahedron 1999, 55, 11039.
2. R.A. Aitken and A.W. Thomas, in Chemistry of the functional groups, Supplement A3, ed. S. Patai, Wiley, New York, 1997, 473.
3. R.A. Aitken, C.E.R. Horsburgh, J.G. McCreadie, S. Seth J. Chem. Soc., Perkin Trans. 1 1994, 1727.
4. R.A. Aitken, H.R. Cooper, A.P. Mehrotra J. Chem. Soc., Perkin Trans. 1 1996, 475.
5. S.A. Abdulganeeva, K.B. Erzhanov Russ. Chem. Rev. 1991, 60, 676.
6. C. Walsh Tetrahedron 1982, 38, 871.
7. P.M. Beart, G.A.R. Johnston Aust. J. Chem. 1972, 25, 1359.
8. A.G. Doutheau, J. Gore and G. Quash, EP 133 407, 1985.
9. B.W. Metcalf, P. Bey, C. Danzin, M.J. Jung, P. Casara, J.P. Vevert J. Am. Chem. Soc. 1978, 100, 2551.
10. P. Casara, C. Danzin, B.W. Metcalf, M.J. Jung J. Chem. Soc., Chem. Commun. 1982, 1190.
11. P. Casara, C. Danzin, B. Metcalf, M. Jung J. Chem. Soc., Perkin Trans. 1 1985, 2201.
12. B.W. Metcalf, P. Casara Tetrahedron Lett. 1975, 3337.
13. A.B. Tabor, A.B. Holmes, R. Baker J. Chem. Soc., Chem. Commun. 1989, 1025.
14. J.R. Burke, R.B. Silverman J. Am. Chem. Soc. 1991, 113, 9329.
15. R.A. Aitken, N. Karodia Chem. Commun. 1996, 2079.
16. H.H. Wasserman, D.S. Ennis, C.A. Blum, V.M. Rotello Tetrahedron Lett. 1992, 33, 6003.
17. H.H. Wasserman, D.S. Ennis, P.L. Power, M.J. Ross J. Org. Chem. 1993, 58, 4785.
18. M.T. Reetz, T.J. Strack, J. Kanand, R. Goddard Chem. Commun. 1996, 733.
19. J.A. Dale, D.L. Dull, H.S. Mosher J. Org. Chem. 1969, 34, 2543.
20. H. Niwa, T. Ogawa, O. Okamoto, K. Yamada Tetrahedron 1992, 48, 10531.
21. M. Smrcina, P. Majer, E. Majerová, T.A. Guerassina, M.A. Eissenstat Tetrahedron 1997, 53, 12867.
22. J.-N. Denis, S. Tchertchian, A. Tomassini, Y. Vallée Tetrahedron Lett. 1997, 38, 5503.
23. K. Yamada, M. Takeda, T. Iwakuma J. Chem. Soc., Perkin Trans. 1 1983, 265.
24. M. Bergmann, L. Zervas Ber. Dtsch. Chem. Ges. 1932, 65, 1192.
25. W. Grassmann, E. Wünsch Chem. Ber. 1958, 91, 462.
26. A. Hantzsch, W.V. Metcalf Ber. Dtsch. Chem. Ges. 1896, 29, 1680.
27. K. Freudenberg, M. Meister Liebigs Ann. Chem. 1935, 518, 86.
28. E. Fischer, W. Axhausen Liebigs Ann. Chem. 1905, 340, 123.
29. F.M.F. Chen, N.L. Benoiton Can. J. Chem. 1987, 65, 1224.
30. M.R. Vernsten, M.B. Moore J. Am. Chem. Soc. 1953, 75, 1320.
31. Y. Kita, J. Haruta, H. Tagawa, Y. Tamura J. Org. Chem. 1980, 45, 4519.
32. L.L. Braun, J.H. Looker J. Am. Chem. Soc. 1958, 80, 359.
33. R.A. Aitken, J.I. Atherton J. Chem. Soc., Perkin Trans. 1 1994, 1281.