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Bis(diamido)‐Bridged Basket Resorcin[4]arenes as Enantioselective Receptors for Amino Acids and Amines
Author(s) -
Botta Bruno,
D'Acquarica Ilaria,
Nevola Laura,
Sacco Fabiola,
Lopez Zara Valbuena,
Zappia Giovanni,
Fraschetti Caterina,
Speranza Maurizio,
Tafi Andrea,
Caporuscio Fabiana,
Letzel Matthias C.,
Mattay Jochen
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700829
Subject(s) - chemistry , enantiomer , diastereomer , stereochemistry , enantioselective synthesis , chirality (physics) , protonation , medicinal chemistry , catalysis , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , ion
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 MS n (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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)