Design, synthesis and preliminary studies on a novel class of chiral receptor for the recognition of amino acid derivatives ¹

Abstract

The design and synthesis of a novel class of chiral receptor for the recognition of amino acid derivatives is described. Moderate enantioselectivity is observed in binding experiments.

References

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; (b) R. P. Bonar-Law and J. K. M. Sanders, J. Am. Chem. Soc., 1995, 117, 259; (c) K. Connors, Binding Constants, Wiley, New York, 1987.
11. (a) H. Gilman and S. Gray, J. Org. Chem., 1958, 23, 1476; (b) G. Bondesson, O. Magnusson and N. E. Stjernstrom, Acta Pharm. Suec., 1978, 15, 337; (c) J. Ashby and C. C. Cook, Adv. Heterocycl. Chem., 1974, 16, 181; (d) A. R. Katritzky and S. Perumal, J. Heterocycl. Chem., 1990, 27, 1737.
12. P. O. Stransky and M. V. Sargent, Adv. Heterocycl. Chem., 1984, 35, 1.
13. (a) M. Regitz, J. Hocker and A. Leiderhegener, Org. Synth., 1973, Coll. vol. V, 179; (b) P. Spagnolo and P. Zanirato, J. Org. Chem., 1982, 47, 3177; (c) E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297; (d) T. W. Green and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 2nd edn., 1991, p. 327.
14. (a) J. M. Muchowski and M. C. Venuti, J. Org. Chem., 1980, 45, 4789; (b) P. Stanetty, H. Koller and M. Mihovolovic, J. Org. Chem., 1992, 57, 6833.
15. C. M. Huwe and S. Blechert, Tetrahedron Lett., 1994, 35, 9533.
16. N. A. Lebel, R. M. Cherluck and E. A. Curtis, Synthesis, 1973, 678.
17. M. Grayson and E. J. Griffith, Topics in Phosphorous Chemistry, Interscience, New York, 1964, vol. 1, p. 17.
18. (a) S. Mori, T. Ayoama and T. Shiori, Chem. Pharm. Bull., 1986, 34, 1524; (b) P. Beak and B. J. Kokko, J. Org. Chem., 1982, 47, 2822.
19. D. A. Evans, D. A. Evrard, S. D. Rychnovsky, T. Fruh, W. G. Whittingham and K. M. DeVries, Tetrahedron Lett., 1992, 33, 1189.
20. (a) T. Shiori, K. Ninomiya and S. Yamada, J. Am. Chem. Soc., 1972, 94, 6203; (b) H. Saikachi and T. Kitagawa, Chem. Pharm. Bull., 1977, 25, 1651; (c) T. Shiori, K. Ninomiya and S. Yamada, Tetrahedron, 1974, 30, 2151.
21. S. Yoo and S. H. Lee, J. Org. Chem., 1994, 59, 6968.
22. I. O. Sutherland, Comprehensive Organic Chemistry, Pergamon, Oxford, 1979, vol. 2, pp. 1084–1087.
23. M. W. Haenel, D. Jakubik, E. Rothenberger and G. Schroth, Chem. Ber., 1991, 124, 1705.
24. E. B. Schwartz, C. B. Knobler and D. J. Cram, J. Am. Chem. Soc., 1992, 114, 10 775.
25. M. W. Haenel, H. Fieseler, D. Jakubik, B. Gabor, R. Goddard and C. Kruger, Tetrahedron Lett., 1993, 34, 2107.
26. A. Alexakis, S. Mutti and P. Mangeney, J. Org. Chem., 1992, 57, 1224.