Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure α,β-amino alcohol groups

Organic Letters

Volumn 6, Issue 8, 2004, Pages 1189-1192

  Zheng, Yan Song ^a   Zhang, Chun ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYISOVALERIC ACID; 2,3 DIBENZOYLTARTARIC ACID; AMINOALCOHOL; CALIXARENE; CARBOXYLIC ACID DERIVATIVE; FUNCTIONAL GROUP; MANDELIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; MOLECULAR RECOGNITION; OPTICS; RACEMIC MIXTURE;

AMINO ALCOHOLS; CALIXARENES; CARBOXYLIC ACIDS; MANDELIC ACIDS; MOLECULAR STRUCTURE; PENTANOIC ACIDS; PHENOLS; STEREOISOMERISM; TARTRATES;

EID: 2542499609     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036122o     Document Type: Article

References (23)

1. Reviews: (a) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 383. (b) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (c) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841.
2. Reviews: (a) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 383. (b) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (c) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841.
3. Reviews: (a) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 383. (b) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (c) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841.
4. (a) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, 1989.
5. (b) Vicence, J.; Böhmer, V. Calixarenes: A Versatile Class of Macrocyclic Compounds; Kluwer Academic Publishers: Norwell, MA, 1991.
6. (a) Kubo, Y.; Maeda, S.; Sumio, T.; Kubo, M. Nature 1996, 382, 522.
7. (b) Lynam, C.; Jennings, K.; Nolan, K.; Kane, P.; McKervey, M. A.; Diamond, D. Anal. Chem. 2002, 74, 59.
8. (c) Grady, T.; Harris, S. J.; Smyth, M. R.; Diamond, D. Anal. Chem. 1996, 68, 3775.
9. (d) Thibodeaux, S. J.; Sanchez Pena, M.; Zhang, Y.; Shamsi, S. A.; Warner, I. M. Chromatographia 1999, 49, 142.
10. (e) Lazzarotto, M.; Sansone, F.; Baldini, L.; Casnati, A.; Cozzini, P.; Ungaro, R. Eur. J. Org. Chem. 2001, 3, 595.
11. (f) Casnati, A.; Fabbi, M.; Peliyyi, N.; Pochini, A.; Sansone, F.; Ungaro, R.; Modugno, E. D.; Taryia, G. Bioorg. Med. Chem. Lett. 1996, 6, 2699.
12. (a) He, Y.; Xiao, Y.; Meng, L.; Zeng, Z.; Wu, X.; Wu, C.-T. Tetrahedron Lett. 2002, 43, 6249.
13. (b) Ito, K.; Noike, M.; Kida, A.; Ohba, Y. J. Org. Chem. 2002, 67, 7519.
14. (c) Okada, Y.; Mizutani, M.; Ishii, F.; Nishimura, J. Enantiomer 2002, 7, 93.
15. (d) Guo, W.; Wang, J.; Wang, C.; He, J.-Q.; He, X.-W.; Cheng, J. P. Tetrahedron Lett. 2002, 43, 5665.
16. (e) Liu, F.; Lu, G.-Y.; He, W.-J.; Wang, Z.-S.; Zhu, L.-J. Chin. J. Chem. 2001, 19, 317.
17. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. Angew. Chem., Int. Ed. 2002, 41, 1924.
18. Zheng, Y. S.; Huang, Z. T. Chin. Chem. Lett. 1997, 8, 685.
19. Bisson, A. P.; Hunter, C. A.; Morales, J. C.; Young, K. Chem. Eur. J. 1998, 4, 845.
20. Goswami, S.; Ghosh, K.; Dasgupta, S. J. Org. Chem. 2000, 65, 1907.
21. (a) Heinrichs, G.; Vial, L.; Lacour, J.; Kubik, S. Chem. Commun. 2003, 1252.
22. (b) Fielding, L. Tetrahedron 2000, 56, 6151.
23. Garcia-Tellado, F.; Albert, J.; Hamilton, A. D. Chem. Commun. 1991, 1761.