Stereoprogrammed direct synthesis of calixarene-based [3]rotaxanes

Organic Letters

Volumn 14, Issue 12, 2012, Pages 3104-3107

  Talotta, Carmen ^a   Gaeta, Carmine ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84862579657     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3011997     Document Type: Article

References (21)

1. Feymann, R. P. Eng. Sci. 1960, 23, 22
2. Drexler, K. E. Science 1992, 255, 268
3. Amabilino, D. A.; Stoddart, J. F. Chem. Rev. 1995, 35, 1154
4. Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines, 2 nd ed.; Wiley-VCH: Weinheim, 2008.
5. Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology; Sauvage, J. P.; Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, 1999.
6. Chen, P.-N.; Lai, C.-C.; Chiu, S.-H. Org. Lett. 2011, 13, 4660
7. Nakazono, K.; Takata, T. Chem.-Eur. J. 2010, 16, 13783
8. Jiang, W.; Winkler, H. D. F.; Schalley, C. A. J. Am. Chem. Soc. 2008, 130, 13852
9. For a recent example of macrolactam-based [3]rotaxane system, see: Fuller, A. M. L.; Leigh, D. A.; Lusby, P. J. J. Am. Chem. Soc. 2010, 132, 4954
10. For recent examples of cucurbituril-based [3]rotaxane systems, see: Wittenberg, J. B.; Costales, M. G.; Zavalij, P. Y.; Isaacs, L. Chem. Commun. 2011, 47, 9420
11. Cheetham, A. G.; Claridge, T. D. W.; Anderson, H. L. Org. Biomol. Chem. 2007, 5, 457
12. Oshikiri, T.; Takashima, Y.; Yamaguchi, H.; Harada, A. Chem.-Eur. J. 2007, 13, 7091
13. Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092
14. Strauss, S. H. Chem. Rev. 1993, 93, 927
15. Nishida, H.; Takada, N.; Yoshimura, M.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1984, 57, 2600
16. Gaeta, C.; Talotta, C.; Farina, F.; Camalli, M.; Campi, G.; Neri, P. Chem.-Eur. J. 2012, 18, 1219
17. Gasa, T. B.; Valente, C.; Stoddart, J. F. Chem. Soc. Rev. 2011, 40, 57
18. We demonstrated that our "superweak anion" approach is a general mode to obtain through-the-annulus threading of scarcely efficient large calix[6]-(9) and -[7]arene(10c) hosts by exploiting the inducing effect of the weakly coordinating TFPB anion. Very recently, our conclusions have been corroborated by Chiu et al., who have shown that the TFPB anion is able to enhance the binding affinity between [24]-crown-8 hosts and dibenzylammonium guests: Chen, N.-C.; Chuang, C.-J.; Wang, L.-Y.; Lai, C.-C.; Chiu, S.-H. Chem.-Eur. J. 2012, 18, 1896
19. Talotta, C.; Gaeta, C.; Pierro, T.; Neri, P. Org. Lett. 2011, 13, 2098
20. Pierro, T.; Gaeta, C.; Talotta, C.; Casapullo, A.; Neri, P. Org. Lett. 2011, 13, 2650
21. MacroModel-9.0/Maestro-4.1 program: Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440