A new approach to enantiopure inherently chiral calix[4]arenes: Determination of their absolute configurations

Organic Letters

Volumn 9, Issue 22, 2007, Pages 4447-4450

  Xu, Zhen Xiang ^a,b   Zhang, Chun ^a   Zheng, Qi Yu ^a   Chen, Chuan Feng ^a   Huang, Zhi Tang ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35948998795     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701714q     Document Type: Article

References (28)

1. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, UK, 1998.
2. Jin, T.; Monde, K. Chem. Commun. 1998, 1357-1358.
3. Dieleman, C.; Steyer, S.; Jeunesse, C.; Matt, D. J. Chem. Soc., Dalton Trans. 2001, 2508-2517.
4. Some examples: (a) Caccamese, S.; Notti, A.; Pappalardo, S.; Parisi, M. F.; Principato, G. Tetrahedron 1999, 55, 5505-5514.
5. (b) Tairov, M. A.; Vysotsky, M. O.; Kalchenko, O. I.; Pirozhenko, V. V.; Kalchenko, V. I. J. Chem. Soc., Perkin Trans. 1 2002, 1405-1411.
6. (c) Caccamese, S.; Bottino, A.; Cunsolo, F.; Parlato, S.; Neri, P. Tetrahedron: Asymmetry 2000, 11, 3103-3112.
7. (d) Hesek, D.; Inoue, Y.; Drew, M. G. B.; Beer, P. D.; Hembury, G. A.; Ishida, H.; Aoki, F. Org. Lett. 2000, 2, 2237-2240.
8. (e) Xu, B.; Carroll, P. J.; Swager, T. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2094-2097.
9. (a) Cao, Y.-D.; Luo, J.; Zheng, Q.-Y.; Chen, C.-F.; Wang, M.-X.; Huang, Z.-T. J. Org. Chem. 2004, 69, 206-208.
10. (b) Luo, J.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Chem. Eur. J. 2005, 11, 5917-5928.
11. (c) Li, S.-Y.; Zheng, Q.-Y.; Chen C.-F.; Huang, Z.-T. Tetrahedron: Asymmetry 2005, 16, 641-645.
12. (d) Mao, R.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. J. Org. Chem. 2005, 70, 7662-7671.
13. (e) Luo, J.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Tetrahedron 2005, 61, 8517-8528.
14. (a) Yakovenko, A. V.; Boyko, V. I.; Danylyuk, O.; Suwinska, K.; Lipkowski, J.; Kalchenko, V. I. Org. Lett. 2007, 9, 1183-1185.
15. (b) Narumi, F.; Hattori, T.; Yamabuki, W.; Kabuto, C.; Kameyama, H. Tetrahedron: Asymmetry 2005, 16, 793-800.
16. (c) Narumi, F.; Hattori, T.; Matsumura, N.; Onodera, T.; Katagiri, H.; Kabuto, C.; Kameyama, H.; Miyano, S. Tetrahedron 2004, 60, 7827-7833.
17. (d) Boyko, V. I.; Shivanyuk, A.; Pyrozhenko, V. V.; Zubatyuk, R. I.; Shishkin, O. V.; Kalchenko, V. I. Tetrahedron Lett. 2006, 47, 7775-7778.
18. Verboom, W.; Bodewes, P. J.; Essen, G. V.; Timmerman, P.; Hummer, G. J. V.; Harkema, S.; Reinhoudt, D. N. Tetrahedron 1995, 51, 499-512.
19. Alemi, A. A.; Shaabani, B.; Dilmaghani, K. A.; Ganjali, S. T. Molecules 2001, 6, 417-423.
20. See the Supporting Information.
21. (a) Halab, L.; Lubell, W. D. J. Am. Chem. Soc. 2002, 124, 2474-2484.
22. (b) Ghasparian, A.; Moehle, K.; Linden, A.; Robinson, J. A. Chem. Commun. 2006, 174-176.
23. 1 = 0.0677 (I > 2σ(I)).
24. About the numbering of carbon atoms in calixarene, see ref 1.
25. Dalla Cort, A.; Mandolini, L.; Pasquini, C.; Schiaffino, L. New J. Chem. 2004, 28, 1198-1199.
26. Wang, J.; Li, H.; Yu, X. H.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4293-4296.
27. 1 = 0.0597 (I > 2σ(I)).
28. For a more recent example, see: Shirakawa, S.; Moriyama, A.; Shimizu, S. Org. Lett. 2007, 9, 3117-3119.