Calix[6]arene threading with weakly interacting tertiary ammonium axles: Generation of chiral pseudorotaxane architectures

Organic Letters

Volumn 17, Issue 4, 2015, Pages 1006-1009

  Talotta, Carmen ^a   De Simone, Nicola Alessandro ^a   Gaeta, Carmine ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84923344336     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00115     Document Type: Article

References (43)

1. Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology; Sauvage, J. P., Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, 1999.
2. Ikeda, T.; Saha, S.; Aprahan, I.; Leung, K. C.-F.; Williams, A.; Deng, W.-Q.; Flood, A. H.; Goddard, W. A.; Stoddart, J. F. Chem.-Asian J. 2007, 2, 76-93
3. Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172-1175
4. Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines, 2 nd ed.; Wiley-VCH: Weinheim, 2008.
5. Saha, S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 77-92
6. Fahrenbach, A. C.; Bruns, C. J.; Cao, D.; Stoddart, J. F. Acc. Chem. Res. 2012, 45, 1581-1592
7. Caballero, A.; Zapata, F.; White, G. N.; Costa, P. J.; Felix, V.; Beer, P. D. Angew. Chem., Int. Ed. 2012, 51, 1876-1880
8. Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375-384
9. Templated Organic Synthesis; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1999.
10. Nakazono, K.; Kuwata, S.; Takata, T. Tetrahedron Lett. 2008, 49, 2397-2401
11. Suzuki, S.; Nakazono, K.; Takata, T. Org. Lett. 2010, 12, 712-715
12. Lu, T.-W.; Chang, C.-F.; Lai, C.-C.; Chiu, S.-H. Org. Lett. 2013, 15, 5742-5745
13. Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092-2095
14. Pierro, T.; Gaeta, C.; Talotta, C.; Casapullo, A.; Neri, P. Org. Lett. 2011, 13, 2650-2653
15. Talotta, C.; Gaeta, C.; Pierro, T.; Neri, P. Org. Lett. 2011, 13, 2098-2101
16. Talotta, C.; Gaeta, C.; Neri, P. Org. Lett. 2012, 14, 3104-3107
17. Gaeta, C.; Talotta, C.; Farina, F.; Teixeira, F. A.; Marcos, P. A.; Ascenso, J. R.; Neri, P. J. Org. Chem. 2012, 77, 10285-10293
18. Gaeta, C.; Talotta, C.; Farina, F.; Camalli, M.; Campi, G.; Neri, P. Chem.-Eur. J. 2012, 18, 1219-1230
19. Gaeta, C.; Talotta, C.; Mirra, S.; Margarucci, L.; Casapullo, A.; Neri, P. Org. Lett. 2013, 15, 116-119
20. Talotta, C.; Gaeta, C.; Qi, Z.; Schalley, C. A.; Neri, P. Angew. Chem., Int. Ed. 2013, 52, 7437-7441
21. Ciao, R.; Talotta, C.; Gaeta, C.; Margarucci, L.; Casapullo, A.; Neri, P. Org. Lett. 2013, 15, 5694-5697
22. Ciao, R.; Talotta, C.; Gaeta, C.; Neri, P. Supramol. Chem. 2014, 26, 569-578
23. Gaeta, C.; Talotta, C.; Neri, P. Chem. Commun. 2014, 50, 9917-9920
24. Talotta, C.; Gaeta, C.; Neri, P. J. Org. Chem. 2014, 79, 9842-9846
25. Chen, N.-C.; Chuang, C.-J.; Wang, L.-Y.; Lai, C.-C.; Chiu, S.-H. Chem.-Eur. J. 2012, 18, 1896-1890
26. Rivera, J. M.; Nartin, T.; Rebek, J., Jr. Science 1998, 279, 1021-1023
27. Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502
28. Pop, A.; Vysotsky, M. O.; Saadioui, M.; Böhmer, V. Chem. Commun. 2003, 1124-1125
29. Xiao, X.; Liu, J.-X.; Fan, Z.-F.; Chen, K.; Zhu, Q.-J.; Xue, S.-F.; Tao, Z. Chem. Commun. 2010, 46, 3741-3743
30. For an example of inherently chiral ammonium-based pseudorotaxane, see: Mobian, P.; Banerji, N.; Bernardinelli, G.; Lacour, J. Org. Biomol. Chem. 2006, 4, 224-231
31. For a pioneering work on the synthesis of cycloenantiomeric rotaxane, see: Yamamoto, C.; Okamoto, Y.; Schmidt, T.; Jäger, R.; Vögtle, F. J. Am. Chem. Soc. 1997, 119, 10547-10548
32. Breault, G. A.; Hunter, C. A.; Mayers, P. C. Tetrahedron 1999, 55, 5265-5293
33. Neal, E. A.; Goldup, S. M. Chem. Commun. 2014, 50, 5128-5142
34. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76
35. Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372-3376
36. Magrans, J. O.; de Mendoza, J.; Pons, M.; Prados, P. J. Org. Chem. 1997, 62, 4518-4520
37. Bifulco, G.; Gomez-Paloma, L.; Riccio, R.; Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2005, 7, 5757-5760
38. Bifulco, G.; Riccio, R.; Gaeta, C.; Neri, P. Chem.-Eur. J. 2007, 13, 7185-7194
39. Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734
40. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
41. Hirose, K. In Analytical Methods in Supramolecular Chemistry; Schalley, C. A., Ed.; Wiley-VCH: Weinheim, 2007; pp 17-54.
42. Yamauchi, K.; Miyawaki, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. Org. Lett. 2010, 12, 1284-1286
43. Hou, X.; Ke, C.; Cheng, C.; Song, N.; Blackburn, A. K.; Sarjeant, A. A.; Botros, Y. Y.; Yang, Y.-W.; Stoddart, J. F. Chem. Commun. 2014, 50, 6196-6199