Design, synthesis and preliminary studies on a novel class of chiral receptor for the recognition of amino acid derivatives

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1998, Pages 457-465

  Tye, Heather ^a   Eldred, Colin ^b   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748665499     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a706843c     Document Type: Article

References (38)

1. Preliminary communication: H. Tye, C. Eldred and M. Wills, Synlett, 1995, 770.
2. H.-J. Schneider, Angew. Chem., Int. Ed. Engl., 1991, 30, 1417.
3. S. Chang and A. D. Hamilton, J. Am. Chem. Soc., 1988, 110, 1318.
4. L. Mussons, C. Raposo, M. Crego, J. Anaya, C. Caballero and J. R. Moran, Tetrahedron Lett., 1994, 35, 7061.
5. C. S. Wilcox, J. C. Adrian Jr., T. H. Webb and F. J. Zawacki, J. Am. Chem. Soc., 1992, 114, 10 189.
6. C. S. Wilcox and T. H. Webb, Chem. Soc. Rev., 1993, 383.
7. J. Rebek, Jr., B. Askew, P. Ballaster and M. Doa, J. Am. Chem. Soc., 1987, 109, 4119.
8. J. R. Moran, M. Crego, A. Partearrogo, C. Raposo, L. Mussons, J. L. Lopez and V. Alcazar, Tetrahedron Lett., 1994, 35, 1435.
9. M. W. Haenel, D. Jakubik, E. Rothenberger and G. Schroth, Chem. Ber., 1991, 124, 1707.
10. (a) M. F. Cristofaro and A. R. Chamberlin, J. Am. Chem. Soc., 1994, 116, 5089;
11. (b) R. P. Bonar-Law and J. K. M. Sanders, J. Am. Chem. Soc., 1995, 117, 259;
12. K. Connors, Binding Constants, Wiley, New York, 1987.
13. (a) H. Gilman and S. Gray, J. Org. Chem., 1958, 23, 1476;
14. (b) G. Bondesson, O. Magnusson and N. E. Stjernstrom, Acta Pharm. Suec., 1978, 15, 337;
15. (c) J. Ashby and C. C. Cook, Adv. Heterocycl. Chem., 1974, 16, 181;
16. (d) A. R. Katritzky, S. Perumal, J. Heterocycl. Chem., 1990, 27, 1737.
17. P. O. Stransky and M. V. Sargent, Adv. Heterocycl. Chem., 1984, 35, 1.
18. (a) M. Regitz, J. Hocker and A. Leiderhegener, Org. Synth., 1973, Coll. vol. V, 179;
19. (b) P. Spagnolo and P. Zanirato, J. Org. Chem., 1982, 47, 3177;
20. (c) E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297;
21. T. W. Green and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 2nd edn., 1991, p. 327.
22. (a) J. M. Muchowski and M. C. Venuti, J. Org. Chem., 1980, 45, 4789;
23. (b) P. Stanetty, H. Koller and M. Mihovolovic, J. Org. Chem., 1992, 57, 6833.
24. C. M. Huwe and S. Blechert, Tetrahedron Lett., 1994, 35, 9533.
25. N. A. Lebel, R. M. Cherluck and E. A. Curtis, Synthesis, 1973, 678.
26. M. Grayson and E. J. Griffith, Topics in Phosphorous Chemistry, Interscience, New York, 1964, vol. 1, p. 17.
27. (a) S. Mori, T. Ayoama and T. Shiori, Chem. Pharm. Bull., 1986, 34, 1524;
28. (b) P. Beak and B. J. Kokko, J. Org. Chem., 1982, 47, 2822.
29. D. A. Evans, D. A. Evrard, S. D. Rychnovsky, T. Fruh, W. G. Whittingham and K. M. DeVries, Tetrahedron Lett., 1992, 33, 1189.
30. (a) T. Shiori, K. Ninomiya and S. Yamada, J. Am. Chem. Soc., 1972, 94, 6203;
31. (b) H. Saikachi and T. Kitagawa, Chem. Pharm. Bull., 1977, 25, 1651;
32. (c) T. Shiori, K. Ninomiya and S. Yamada, Tetrahedron, 1974, 30, 2151.
33. S. Yoo and S. H. Lee, J. Org. Chem., 1994, 59, 6968.
34. I. O. Sutherland, Comprehensive Organic Chemistry, Pergamon, Oxford, 1979, vol. 2, pp. 1084-1087.
35. M. W. Haenel, D. Jakubik, E. Rothenberger and G. Schroth, Chem. Ber., 1991, 124, 1705.
36. E. B. Schwartz, C. B. Knobler and D. J. Cram, J. Am. Chem. Soc., 1992, 114, 10775.
37. M. W. Haenel, H. Fieseler, D. Jakubik, B. Gabor, R. Goddard and C. Kruger, Tetrahedron Lett., 1993, 34, 2107.
38. A. Alexakis, S. Mutti and P. Mangeney, J. Org. Chem., 1992, 57, 1224.