Structurally simple, modular amino alcohols for the recognition of carboxylic acids. Application to the development of a new chiral solvating agent

Organic Letters

Volumn 7, Issue 24, 2005, Pages 5485-5487

  Cuevas, Félix ^a   Ballester, Pablo ^a,c   Pericàs, Miquel A ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28844472494     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052490b     Document Type: Article

References (18)

1. (a) Yoshizawa, M.; Kusukawa, T.; Kawano, M.; Ohhara, T.; Tanaka, I.; Kurihara, K.; Niimura, N.; Fujita, M. J. Am. Chem. Soc. 2005, 127, 2798-2799.
2. (b) Brotin, T.; Lesage, A.; Emsley, L.; Collet, A. J. Am. Chem. Soc. 2000, 122, 1171-1174.
3. (c) Helgeson, R. C.; Paek, K.; Knobler, C. B.; Maverick, E. F.; Cram, D. J. J. Am. Chem. Soc. 1996, 118, 5590-5604.
4. (d) Kerckhoffs, J.; van Leeuwen, F. W. R.; Spek, A. L.; Kooijman, H.; Crego-Calama, M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2003, 42, 5717-5722.
5. (a) Atwood, J. L.; Szumna, A. J. Am. Chem. Soc. 2002, 124, 10646-10647,
6. (b) Rudkevich, D. M.; Hilmersson, G.; Rebek, J. J. Am. Chem. Soc. 1998, 120, 12216-12225.
7. Garric, J.; Leger, J. M.; Huc, I. Angew. Chem., Int. Ed. 2005, 44, 1954-1958 and refs 13-21 cited therein.
8. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947-8948.
9. See for instance: Fontes, M.; Verdaguer, X.; Solà, L.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2004, 69, 2532-2543 and references therein
10. Rodriguez-Escrich, S.; Popa, D.; Jimeno, C.; Vidal-Ferran, A.; Pericas, M. A. Org. Lett. 2005, 7, 3829-3832.
11. Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864.
12. (a) Parker, D. Chem. Rev. 1991, 91, 1441-1457.
13. (b) Wenzel, T. J.; Wilcox, J. D. Chirality 2003, 15, 256-70.
14. For recent examples of CSA for carboxylic acids, see: (a) Yang, D.; Li, X.; Fan, Y.-F.; Zhang, D.-W. J. Am. Chem. Soc. 2005, 127, 7996-7997.
15. (b) Zheng, Y. S.; Zhang, C. Org. Lett. 2004, 6, 1189-1192.
16. (c) Port, A.; Virgili, A.; Alvarez-Larena, A.; Piniella, J. F. Tetrahedron: Asymmetry 2000, 11, 3747-3757.
17. Titration data were analyzed by fitting to a simple 1:1 binding isotherm using the software SPECFIT 3.0: (a) Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1985, 32, 95-101.
18. (b) Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1986, 33, 943-951. Job plots are also in agreement with the exclusive formation of 1:1 stoichiometry complexes.