Polyfunctionalized macrocycles demonstrate enantioselective and ditopic binding properties

Chemical Communications

Volumn , Issue 26, 2005, Pages 3319-3321

  Gong, Jiachang ^a   Gibb, Bruce C ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; CATION; MACROCYCLIC COMPOUND;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOSELECTIVITY; MOLECULAR RECOGNITION; STEREOCHEMISTRY;

EID: 22544473621     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b501774b     Document Type: Article

References (31)

1. For reviews, see: (a) T. H. Webb and C. S. Wilcox, Chem. Soc. Rev., 1993, 22, 383;
2. (b) X. X. Zhang, J. S. Bradshaw and R. M. Izatt, Chem. Rev., 1997, 97, 3313;
3. (c) L. Pu, Chem. Rev., 2004, 104, 1687;
4. (d) H. Ogoshi and T. Mizutani, Acc. Chem. Res., 1998, 31, 81.
5. (a) L. Siracusa, F. M. Hurley, S. Dresen, L. J. Lawless, M. N. Pérez-Payán and A. P. Davis, Org. Lett., 2002, 4, 4639;
6. (b) J. L. Sessler and A. Andrievshy, Chem. Eur. J., 1998, 4, 159;
7. (c) G. J. Pernía, J. D. Kilburn and M. Rowley, Chem. Commun., 1995, 305;
8. (d) L. J. Lawless, A. G. Blackburn, A. J. Ayling, M. N. Pérez-Payán and A. P. Davis, J. Chem. Soc., Perkin Trans. 1, 2001, 1329.
9. (a) Y. Kubo, S. Maeda, S. Tokita and M. Kubo, Nature, 1996, 382, 522;
10. (b) L. Zhu and E. V. Anslyn, J. Am. Chem. Soc., 2004, 126, 3676.
11. P. Breccia, M. V. Gool, R. Pérez-Fernández, S. Martín-Santamaríz, F. Gago, P. Prados and J. de Mendoza, J. Am. Chem. Soc., 2003, 125, 8270.
12. Y. Murakami, J.-I. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 1996, 96, 721.
13. J. Gong and B. C. Gibb, Chem. Commun., 2005, 1393.
14. For reviews of ditopic hosts see: (a) B. D. Smith and J. M. Mahoney, in Encyclopaedia of Supramolecular Chemistry, ed. J. L. Atwood and J. W. Steed, Pergamon, New York, 2004, pp. 1291-1294;
15. (b) P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed., 2001, 40, 486;
16. (c) G. J. Kirkovits, J. A. Shriver, P. A. Gale and J. L. Sessler, J. Inclusion Phenom. Mol. Recognit. Chem., 2001, 41, 69;
17. P. A. Gale, Coord. Chem. Rev., 2003, 240, 191.
18. See also references in ref. 6. 8 For enantioselective recognition of zwitterionic amino acids see: (a) A. Metzger, K. Gloe, H. Stephan and F. P. Schmidtchen, J. Org. Chem., 1996, 61, 2051;
19. (b) H. Tsukube, J.-I. Uenishi, T. Kanatani, H. Itoh and O. Yonemitsu, Chem. Commun., 1996, 477;
20. (c) B. Escuder, A. E. Rowan, M. C. Feiters and R. J. M. Nolte, Tetrahedron, 2004, 60, 291;
21. (d) A. Galán, D. Andreu, A. M. Echavarren, P. Prados and J. de Mendoza, J. Am. Chem. Soc., 1992, 114, 1511.
22. For enantioselective recognition of amino acids via the amino group see: (a) W.-L. Wong, K.-H. Huang, P.-F. Teng, C.-S. Lee and H.-L. Kwong, Chem. Commun., 2004, 384;
23. (b) J.-S. You, X.-Q. Yu, G.-L. Zhang, Q.-X. Xiang, J.-B. Lan and R.-G. Xie, Chem. Commun., 2001, 1816;
24. (c) S.-G. Kim, K.-H. Kim, Y. K. Kim, S. K. Shin and K. H. Ahn, J. Am. Chem. Soc., 2003, 125, 13819;
25. (d) T. Grawe, T. Schrader, P. Finocchiaro, G. Consiglio and S. Failla, Org. Lett., 2001, 3, 1597;
26. (e) K. Araki, K. Inada and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 72.
27. For enantioselective recognition of amino acids via the carboxylate group see: (a) R. J. Fitzmaurice, G. M. Kyne, D. Douheret and J. D. Kilburn, J. Chem. Soc., Perkin Trans. 1, 2002, 841;
28. (b) A. I. Oliva, L. Simón, F. M. Muñiz, F. Sanz and J. R. Morán, Org. Lett., 2004, 6, 1155;
29. (c) A. I. Oliva, L. Simón, J. V. Hernández, F. M. Muñiz, A. Lithgow, A. Jiménez and J. R. Morán, J. Chem. Soc., Perkin Trans. 2, 2002, 1050;
30. (d) S. Rossi, G. M. Kyne, D. L. Turner, N. J. Wells and J. D. Kilburn, Angew. Chem., Int. Ed., 2002, 41, 4233.
31. E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1984.