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.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Botta, Bruno; D'Acquarica, Flaria; Nevola, Laura; Sacco, Fabiola; Lopez, Zara Valbuena; Zappia, Giovanni; Fraschetti, Caterina; Speranza, Maurizio; Tafi, Andrea; Caporuscio, Fabiana; Letzel, MatthiasUniBi; Mattay, JochenUniBi
Alle
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.
Stichworte
host-guest systems; macrocycles; chirality; resorcinarenes
Erscheinungsjahr
2007
Zeitschriftentitel
European Journal of Organic Chemistry
Band
2007
Ausgabe
36
Seite(n)
5995-6002
ISSN
1434-193X
eISSN
1099-0690
Page URI
https://pub.uni-bielefeld.de/record/1630972

Zitieren

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. https://doi.org/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.

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