A novel synthesis of didehydroamino acid esters from azomethine ylides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1998, Pages 2837-2846

  Groundwater, Paul W ^a   Sharif, Toqir ^b   Arany, Andrea ^c   Hibbs, David E ^b   Hursthouse, Michael B ^b   Garnett, Ian ^a   Nyerges, Miklos ^d  

^a UNIVERSITY OF SUNDERLAND   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF VETERINARY MEDICINE   (Hungary)

^d BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748647038     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803695k     Document Type: Article

References (34)

1. (a) T. J. Nitz, E. M. Holt, B. Rubin and C. H. Stammer, J. Org. Chem., 1981, 46, 2667;
2. (b) M. D. Grim, V. Chauhan, Y. Shimohigashi, A. J. Kolar and C. H. Stammer, J. Org. Chem., 1981, 46, 2671;
3. (c) T. V. Rajan Babu, T. A. Ayers, G. A. Halliday, K. K. You and J. C. Calabrese, J. Org. Chem., 1997, 62, 6012.
4. For a review see, W. S. Knowles, Acc. Chem. Res., 1983, 16, 106.
5. Recent example: A. S. C. Chan, W. H. Hu, C.-C. Pai, C.-P. Lau, Y. Z. Jiang, A. Q. Mi, M. Yan, J. Sun, R. L. Lou and J. G. Deng, J. Am. Chem. Soc., 1997, 119, 9570.
6. (a) C. H. Stammer, Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, John Wright and Sons Ltd., London, 1982, vol. 6, p. 33;
7. (b) H. G. Floss and J. C. Vederas, in New Comprehensive Biochemistry, Vol. 3: Stereochemistry, ed. C. Tamm, Elsevier Science, Amsterdam, 1982, p. 161.
8. T. Takita, T. Tamura and H. Taniyama, J. Biochem., 1977, 81, 1759.
9. See, for example, (a) M. J. Burk, J. G. Allen, W. F. Kiesman and K. M. Stoffan, Tetrahedron Lett., 1997, 38, 1309;
10. (b) U. Schmidt, A. Lieberknecht and J. Wild, Synthesis, 1988, 159 and references therein;
11. (c) R. Grigg and J. Kemp, J. Chem. Soc., Chem. Commun., 1977, 125.
12. P. W. Groundwater, T. Sharif, A. Arany, D. E. Hibbs, M. B. Hursthouse and M. Nyerges, Tetrahedron Lett., 1998, 39, 1433.
13. (a) P. W. Groundwater, C. Struthers-Semple and J. T. Sharp, J. Chem. Soc., Chem. Commun., 1987, 1367;
14. (b) P. W. Groundwater and J. T. Sharp, Tetrahedron, 1992, 48, 7951;
15. (c) P. W. Groundwater, A. J. Morton and R. Salter, J. Chem. Soc., Chem. Commun., 1993, 1789.
16. R. Grigg and V. Sridharan, in Advances in Cycloaddition, ed. D. P. Curran, JAI Press, 1993, vol. 3, p. 161.
17. W. Nagata, T. Wakabayashi and Y. Hayase, Org. Synth., 1988, Coll. Vol. VI, 448.
18. R. Grigg, Chem. Soc. Rev., 1987, 16, 89.
19. R. Grigg, H. Q. N. Gunaratne and J. Kemp, J. Chem. Soc., Perkin Trans. 1, 1984, 41.
20. R. Grigg and H. Q. N. Gunaratne, J. Chem. Soc., Chem. Commun., 1982, 384.
21. K. Amornraksa, D. Barr, G. Donegan, R. Grigg, P. Ratananukul and V. Sridharan, Tetrahedron, 1989, 45, 4649.
22. H. Cerecetto, R. Di Maio, M. Gonzalez and G. Seoane, Heterocycles, 1997, 45, 2023.
23. M. Nyerges, M. Rudas, G. Toth, B. Herenyi, I. Bitter and L. Toke, Tetrahedron, 1995, 51, 13 321.
24. O. Tsuge, S. Kanemasa, T. Yamada and K. Matsuda, J. Org. Chem., 1987, 52, 2523.
25. D. D. Perrin and W. L. F. Armarego, Purification of Organic Compounds, 3rd edn., Pergamon Press, Oxford, 1988.
26. O. Tsuge, S. Kanemasa, M. Ohe, K. Yorozu, S. Takenaka and K. Ueno, Chem. Lett., 1986, 1271.
27. M. A. El Maghraby and K. M. Hassan, Indian J. Chem., 1973, 11, 1205.
28. J.-P. Genet, S. Juge, S. Achi, S. Mallart, J. Montes and G. Levif, Tetrahedron, 1988, 44, 5263.
29. J. A. Darr, S. R. Drake and M. B. Hursthouse, Inorg. Chem., 1993, 32, 5704.
30. G. M. Sheldrick, Acta. Crystallogr., Sect. A, 1990, 46, 467.
31. G. M. Sheldrick, SHELXL-93: Program for Crystal Structure Refinement, University of Göttingen, Germany.
32. D. G. Farnum, M. Ghandi, S. Raghu and T. Reitz, J. Org. Chem., 1982, 47, 2598.
33. O. Mamoun, H. Benhaoua, R. Danion-Bougot and D. Danion, Synth. Commun., 1995, 25, 1295.
34. T. Moriya, K. Matsumoto and M. Miyoshi, Synthesis, 1981, 915.