Enantioselective recognition with C3-symmetric cage-like receptors in solution and on a stationary phase

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 10, 1997, Pages 1891-1900

  Pieters, Roland J ^a   Cuntze, Jens ^a   Bonnet, Muriel ^a   Diederich, François ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347802782     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702627g     Document Type: Article

References (76)

1. (a) J.-M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995;
2. (b) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen and D. M. Gordon, Acc. Chem. Res., 1995, 28, 37;
3. (c) J. Rebek, Jr., Chem. Soc. Rev., 1996, 25, 255;
4. (d) D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1154;
5. (e) A. J. Kirby, Angew. Chem., Int. Ed. Engl., 1996, 35, 707;
6. (f) Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 1996, 96, 721;
7. (g) Tetrahedron Symposium-In-Print on Molecular Recognition, ed. A. D. Hamilton, Tetrahedron, 1995, 51, 343.
8. T. H. Webb and C. S. Wilcox, Chem. Soc. Rev., 1993, 22, 383.
9. See for example the complexes formed between monosaccharides and bacterial carbohydrate transport proteins: F. A. Quiocho, Pure Appl. Chem., 1989, 61, 1293.
10. For a preliminary communication of parts of this work, see: R. J. Pieters and F. Diederich, Chem. Commun., 1996, 2255.
11. (a) C. Seel and F. Vögtle, Angew. Chem., Int. Ed. Engl., 1992, 31, 528;
12. (b) D. J. Cram and J. M. Cram, in Container Molecules and Their Guests; Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1994;
13. (c) Y. Murakami, O. Hayashida and Y. Nagai, J. Am. Chem. Soc., 1994, 116, 2611;
14. (d) F. Diederich, in Cyclophanes: Monographs in Supramolecular Chemistry, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1991.
15. (a) J. Rebek, Jr., Angew. Chem., Int. Ed. Engl., 1990, 29, 245;
16. (b) A. D. Hamilton, in Bioorganic Chemistry Frontiers, ed. H. Dugas, Springer Verlag, Berlin, 1991, vol. 2, pp. 115-174.
17. (a) J.-I. Hong, S. K. Namgoong, A. Bernardi and W. C. Still, J. Am. Chem. Soc., 1991, 113, 5111; S. S. Yoon and W. C. Still, J. Am. Chem. Soc., 1993, 115, 823;
18. (a) J.-I. Hong, S. K. Namgoong, A. Bernardi and W. C. Still, J. Am. Chem. Soc., 1991, 113, 5111; S. S. Yoon and W. C. Still, J. Am. Chem. Soc., 1993, 115, 823;
19. (b) K. S. Jeong, T. Tjivikua, A. Muehldorf, G. Deslongchamps, M. Famulok and J. Rebek, Jr., J. Am. Chem. Soc., 1991, 113, 201;
20. (c) J. Cuntze, L. Owens, V. Alcázar, P. Seiler and F. Diederich, Helv. Chim. Acta, 1995, 78, 367;
21. (d) R. P. Bonar-Law, L. G. Mackay, C. J. Walter, V. Marvaux and J. K. M. Sanders, Pure Appl. Chem., 1994, 66, 803.
22. (a) W. H. Pirkle and T. C. Pochapsky, Chem. Rev., 1989, 89, 347;
23. (b) G. D. Y. Sogah and D. J. Cram, J. Am. Chem. Soc., 1979, 101, 3035.
24. (a) P. Ballester, A. Costa, P. M. Deyà, J. F. González, M. C. Rotger and G. Deslongchamps, Tetrahedron Lett., 1994, 35, 3813;
25. (b) S. Kohmoto, D. Fukui, T. Nagashima, K. Kishikawa, M. Yamamoto and K. Yamada, Chem. Commun., 1996, 1869;
26. (c) A. P. Davis and J. J. Walsh, Chem. Commun., 1996, 449;
27. (d) F. Vögtle, I. Michel, R. Berscheid, M. Nieger, K. Rissanen, S. Kotila, K. Airola, N. Armaroli, M. Maestri and V. Balzani, Liebigs. Ann., 1996, 1697;
28. (e) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart and D. J. Williams, Angew. Chem., Int. Ed. Engl., 1997, 36, 59.
29. (a) W. A. Nugent, J. Am. Chem. Soc., 1992, 114, 2768;
30. (b) H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura and M. Shibasaki, J. Am. Chem. Soc., 1993, 115, 10372.
31. (a) A Practical Approach to Chiral Separations by Liquid Chromatography, ed. G. Subramanian, VCH, Weinheim, 1994;
32. (b) Chiral Separations. Fundamental Aspects and Applications, ed. W. Lindner, J. Chromatogr. A, 1994, 666, 1-654;
33. (c) S. G. Allenmark, Chromatographic Enantioseparation, Horwood, New York, 1991;
34. (d) Chiral Separations by HPLC, ed. A. M. Krstulovic, Horwood, Chichester, 1989;
35. (e) E. Yashima, C. Yamamoto and Y. Okamoto, J. Am. Chem. Soc., 1996, 118, 4036.
36. F. Gasparrini, D. Misiti, C. Villani, A. Borchardt, M. T. Burger and W. C. Still, J. Org. Chem., 1995, 60, 4314.
37. (a) S. C. Zimmerman and K. W. Saionz, J. Am. Chem. Soc., 1995, 117, 1175;
38. (b) S. C. Zimmerman and W.-S. Kwan, Angew. Chem., Int. Ed. Engl., 1995, 34, 2404;
39. (c) M. Martín, C. Raposo, M. Almaraz, M. Crego, C. Caballero, M. Grande and J. R. Morán, Angew. Chem., Int. Ed. Engl., 1996, 35, 2386.
40. J. Cuntze and F. Diederich, Helv. Chim. Acta, 1997, 80, 897.
41. For the complexation of various amino acid derivatives, see: (a) H.-J. Schneider, Angew. Chem., Int. Ed. Engl., 1993, 32, 848;
42. (b) Y. Kuroda, Y. Kato, T. Higashioji, J. Hasegawa, S. Kawanami, M. Takahashi, N. Shiraishi, K. Tanabe and H. Ogoshi, J. Am. Chem. Soc., 1995, 117, 10950;
43. (c) G. J. Pernía, J. D. Kilburn, J. W. Essex, R. J. Mortishire-Smith and M. Rowley, J. Am. Chem. Soc., 1996, 118, 10220;
44. (d) M. F. Cristofaro and A. R. Chamberlin, J. Am. Chem. Soc., 1994, 116, 5089;
45. (e) M. R. Carrasco and W. C. Still, Chem. Biol., 1995, 2, 205;
46. (f) M. J. Crossley, L. G. Mackay and A. C. Try, J. Chem. Soc., Chem. Commun., 1995, 1925;
47. (g) K. Konishi, K. Yahara, H. Toshishige, T. Aida and S. Inoue, J. Am. Chem. Soc., 1994, 116, 1337;
48. (h) M. Asakawa, C. L. Brown, D. Pasini, J. F. Stoddart and P. G. Wyatt, J. Org. Chem., 1996, 61, 7234.
49. (a) Excitatory Amino Acid Receptors: Design of Agonists and Antagonists, ed. P. Krogsgaard-Larsen and J. J. Hansen, Ellis Horwood, New York, 1992;
50. (b) Frontiers in Excitatory Amino Acid Research, ed. E. A. Cavalheiro, J. Lehmann and L. Turski, Alan R. Liss, New York, 1988;
51. (c) The NMDA Receptor, ed. J. C. Watkins and G. L. Collingridge, Oxford University Press, Oxford, 1989.
52. E. Martinborough, T. Mordasini-Denti, P. P. Castro, T. B. Wyman, C. B. Knobler and F. Diederich, Helv. Chim. Acta, 1995, 78, 1037.
53. K. Bernhauer, P. Müller and F. Neiser, J. Prakt. Chem., 1936, 145, 301.
54. N. Horiuchi, J. Huff and J. Rebek, Jr., Tetrahedron Lett., 1990, 36, 5121.
55. A. Wallon, U. Werner, W. M. Müller, M. Nieger and F. Vögtle, Chem. Ber., 1990, 123, 859.
56. (a) G. Chang, W. C. Guida and W. C. Still, J. Am. Chem. Soc., 1989, 111, 4379;
57. (b) M. Saunders, K. N. Houk, Y.-D. Wu, W. C. Still, M. Lipton, G. Chang and W. C. Guida, J. Am. Chem. Soc., 1990, 112, 1419.
58. W. C. Still, Columbia University, New York, 1995.
59. D. Q. McDonald and W. C. Still, Tetrahedron Lett., 1992, 33, 7743.
60. W. C. Still, A. Tempczyk, R. C. Hawley and T. Hendrickson, J. Am. Chem. Soc., 1990, 112, 6127.
61. S. H. Gellman, G. P. Dado, G.-B. Liang and B. R. Adams, J. Am. Chem. Soc., 1991, 113, 1164.
62. B. J. Whitlock and H. W. Whitlock, J. Am. Chem. Soc., 1994, 116, 2301.
63. K. T. Chapman and W. C. Still, J. Am. Chem. Soc., 1989, 111, 3075.
64. A. E. Derome, Modern NMR Techniques for Chemistry Research, Pergamon Press, Oxford, 1987.
65. J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates, and Resolutions, Wiley, New York, 1981.
66. S. Abdalla, E. Bayer and H. Frank, Chromatographia, 1987, 23, 83.
67. A. Tambuté and A. Bégos, New. J. Chem., 1989, 13, 625.
68. P. Salvadori, D. Pini, C. Rosini, C. Bertucci and G. Uccello-Barretta, Chirality, 1992, 4, 43.
69. B. Winter-Werner, F. Diederich and V. Gramlich, Helv. Chim. Acta, 1996, 79, 1338.
70. G. E. Berendsen and L. de Galan, J. Liq. Chromatogr., 1978, 1, 561.
71. H. Brunner and W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, VCH, Weinheim, 1993, vols. 1 and 2.
72. (a) D. J. Cram and J. M. Cram, Acc. Chem. Res., 1978, 11, 8;
73. (b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens and F. Diederich, J. Org. Chem., 1994, 59, 3151, and refs. cited therein;
74. (c) U. Neidlein and F. Diederich, Chem. Commun., 1996, 1493.
75. D. Marcovici-Mizrahi, H. E. Gottlieb, V. Marks and A. Nudelman, J. Org. Chem., 1996, 61, 8402.
76. Associate V. 1.6, B. R. Peterson, PhD Thesis, University of California at Los Angeles, 1994.