Chiral self-discrimination in a M3L2 subphthalocyanine cage

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14522-14523

  Claessens, Christian G ^a   Torres, Tomás ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; SUBPHTHALOCYANINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; ISOMER; NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0037065299     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028705j     Document Type: Article

References (38)

1. Claessens, C. G.; González-Rodríguez, D.; Torres, T. Chem. Rev. 2002, 102, 835-853.
2. (a) Claessens, C. G.; Torres, T. Angew. Chem., Int. Ed. 2002, 41, 2561-2565.
3. (b) Takamitsu, F.; Stork, J. R.; Potucek, R. J.; Olmstead, M. M.; Noll, B. C.; Kobayashi, N.; Durfee, W. S. ibid. 2002, 41, 2565-2568.
4. Claessens, C. G.; Torres, T. Eur. J. Org. Chem. 2000, 1603-1607.
5. (a) González-Rodríguez, D.; Torres, T.; Guldi, D. M.; Rivera, J.; Echegoyen, L. Org. Lett. 2002, 4, 335-338.
6. (b) del Rey, B.; Keller, U.; Torres, T.; Rojo, G.; Agulló-López, F.; Nonell, S.; Marti, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1998, 120, 12808-12817.
7. As a matter of fact [M] is [M,M,M] and [P] is [P,P,P], the key dihedric angles being the ones formed by Cl-B-N-C; see: (a) Claessens, C. G.; Torres, T. Tetrahedron Lett. 2000, 41, 6361-6365. (b) Kobayashi, N.; Nonomura, T. Tetrahedron Lett. 2002, 43, 4253-4255.
8. As a matter of fact [M] is [M,M,M] and [P] is [P,P,P], the key dihedric angles being the ones formed by Cl-B-N-C; see: (a) Claessens, C. G.; Torres, T. Tetrahedron Lett. 2000, 41, 6361-6365. (b) Kobayashi, N.; Nonomura, T. Tetrahedron Lett. 2002, 43, 4253-4255.
9. (a) Collet, A. In Comprehensive Supramolecular Chemistry: Molecular Recognition: Receptors for Molecular Guests; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vötgle, F., Eds.; Elsevier: New York, 1996; Vol. 2, pp 325-365.
10. (b) Pieters, R. J.; Cuntze, J.; Bonnet, M.; Diederich, F. J. Chem. Soc., Perkin Trans. 2 1997, 1891-1900.
11. (c) Moberg, C. Angew. Chem., Int. Ed. 1998, 37, 248-268.
12. (d) Kim, S.-G.; Kim, K.-H.; Jung, J.; Shin, S. K.; Ahn, K. H. J. Am. Chem. Soc. 2002, 124, 591-596.
13. (e) Lesot, P.; Merlet, D.; Sarfati, M.; Courtieu, J.; Zimmermann, H.; Luz, Z. J. Am. Chem. Soc. 2002, 124, 10071-10082.
14. (a) Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. 1998, 37, 932-935.
15. (b) Albrecht, M.; Shneider, M.; Röttele, H. Angew. Chem., Int. Ed. 1999, 38, 557-559.
16. (c) Ismagilov, R. F.; Schwartz, A.; Bowden, N.; Whitesides, G. M. Angew. Chem., Int. Ed. 2002, 41, 652-654.
17. (d) Kuhnle, A.; Linderoth, T. R.; Hammer, B.; Besenbacher, F. Nature (London) 2002, 415, 891-893.
18. (e) Kim, H.-J.; Moon, D.; Soo Lah, M.; Hong, J.-I. Angew. Chem., Int. Ed. 2002, 41, 3174-3177.
19. (a) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
20. (b) Hasenknopf, B.; Lehn, J.-M.; Baum, G.; Fenske, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 1397-1400.
21. (c) Kim, T. W.; Lah, M. S.; Hong, J.-I. Chem. Commun. 2001, 743-744.
22. (d) Alkorta, I.; Elguero, J. J. Am. Chem. Soc. 2002, 124, 1488-1493.
23. Zhong, Z.; Ikeda, A.; Shinkai, S.; Sakamoto, S.; Yamaguchi, K. Org. Lett. 2001, 3, 1085-1087.
24. (a) Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975-982.
25. (b) Fujita M. In Molecular Self-Assembly: Organic Versus Inorganic Approaches; Fujita M., Ed.; Springer-Verlag: Berlin, 2000; pp 177-201.
26. (c) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908.
27. (d) Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3483-3537.
28. (e) Holliday, B. J.; Mirkin, C. A. Angew. Chem., Int. Ed. 2001, 40, 2022-2043.
29. (f) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. Seidel S. R.; Stang, P. J. Acc. Chem. Res. 2002, ASAP article, August 21, 2002.
30. (f) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508. Seidel S. R.; Stang, P. J. Acc. Chem. Res. 2002, ASAP article, August 21, 2002.
31. (a) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613-615.
32. (b) Fujita, M.; Fujita, N.; Ogura, K.; Yamaguchill, K. Nature (London) 1999, 400, 52-55.
33. (c) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239-10240.
34. (d) Bretonniere, Y.; Mazzanti, M.; Wietzke, R.; Pecaut, J. Chem. Commun. 2000, 1543-1544.
35. (e) Radhakrishnan, U.; Schweiger, M.; Stang, P. J. Org. Lett. 2001, 3, 3141-3143.
36. (f) Sun, W.-Y.; Fan, J.; Okamura, T.-A.; Xie, J.; Yu, K.-B.; Ueyama, N. Chem. Eur. J. 2001, 7, 2557-2562.
37. Nicolaou, K. C.; Hepworth, D.; King, N, P.; Finlay, M. R. V.; Scarpelli, R.; Pereira, M. M. A.; Bigot, A.; Werschkun, B.; Winssinger, N. Chem. Eur. J. 2000, 6, 2783-2800.
38. Pirkle, W. H.; Selness, S. R. J. Org. Chem. 1995, 60, 3252-3256.