Enantioselective Recognition of Calix[4]arene Derivative Bearing Bicyclic Guanidinium for D/L Amino Acid Zwitterions

The p-tetra-tert-butyl calix[4] arene derivatives (3 and 4) with (5,5) chiral bicyclic guanidinium, as the receptors of amino acid zwitterions, have been synthesized via a O-alkylation reaction of p-tetra-tert-butyl calix [4] arene with cbJoromethyl chiral bicyclic guanidinium 2 in the presence of anhydrous K2CO3 in acetonitrile. The results obtained from liquid-liquid competitive extraction experiments indicate that the two receptors may selectively recognize L-aromatic amino acids, and that the enantioselective recognizability of the receptor 4 with two chiral bicyclic guanidinium units reachs up to about 90% for L-Phe.

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