Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines

Botta B, D'Acquarica F, Nevola L, Sacco F, Lopez ZV, Zappia G, Fraschetti C, Speranza M, Tafi A, Caporuscio F, Letzel M, et al. (2007)
European Journal of Organic Chemistry 2007(36): 5995-6002.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
On the research avenue opened by the rigidified double-spanned resorcin[4]arene 1, we have synthesized both enantiomers of the two chiral basket resorcin[4]arenes 3 and 4, each containing two 1,2-diaminocyclohexane and 1,2-diphenylethylenediamine bridges, respectively. In the new compounds, the aromatic rims assume the expected flattened cone arrangement, whereas two different conformations, tentatively designated as "open wings" and "folded wings", were attributed to the bridge substituents according to molecular modeling studies. In MSn (ESI) experiments, the proton-bonded diastereomeric [4.H.A](+) complexes with amino acidic guests (A) exhibited a pronounced selectivity towards the enantiomers of tyrosine methyl ester (tyr(OMe)) and amphetamine (amph), whereas the chirality of tryptophan (trp) was ineffective. Moreover, a kinetic study on the base-induced displacement of the guest revealed that the L-tyr(OMe) (and L-amph) enantiomer is faster displaced from the heterochiral [4.H.L-tyr(OMe)](+) (or [ent-4.H.L-amph](+)) complex than from the homochiral [ent-4.H.L-tyr(OMe)](+) (or [4.H.L-amph](+)) one. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007.
Erscheinungsjahr
Zeitschriftentitel
European Journal of Organic Chemistry
Band
2007
Zeitschriftennummer
36
Seite
5995-6002
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eISSN
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Botta B, D'Acquarica F, Nevola L, et al. Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines. European Journal of Organic Chemistry. 2007;2007(36):5995-6002.
Botta, B., D'Acquarica, F., Nevola, L., Sacco, F., Lopez, Z. V., Zappia, G., Fraschetti, C., et al. (2007). Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines. European Journal of Organic Chemistry, 2007(36), 5995-6002. doi:10.1002/ejoc.200700829
Botta, B., D'Acquarica, F., Nevola, L., Sacco, F., Lopez, Z. V., Zappia, G., Fraschetti, C., Speranza, M., Tafi, A., Caporuscio, F., et al. (2007). Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines. European Journal of Organic Chemistry 2007, 5995-6002.
Botta, B., et al., 2007. Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines. European Journal of Organic Chemistry, 2007(36), p 5995-6002.
B. Botta, et al., “Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines”, European Journal of Organic Chemistry, vol. 2007, 2007, pp. 5995-6002.
Botta, B., D'Acquarica, F., Nevola, L., Sacco, F., Lopez, Z.V., Zappia, G., Fraschetti, C., Speranza, M., Tafi, A., Caporuscio, F., Letzel, M., Mattay, J.: Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines. European Journal of Organic Chemistry. 2007, 5995-6002 (2007).
Botta, Bruno, D'Acquarica, Flaria, Nevola, Laura, Sacco, Fabiola, Lopez, Zara Valbuena, Zappia, Giovanni, Fraschetti, Caterina, Speranza, Maurizio, Tafi, Andrea, Caporuscio, Fabiana, Letzel, Matthias, and Mattay, Jochen. “Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines”. European Journal of Organic Chemistry 2007.36 (2007): 5995-6002.