Synthesis and complexing properties of a chiral macrocyclic molecular receptor with convergent binding sites

Abstract

Two novel hosts: 15-crown-5 and N-benzyl-aza-15-crown-5 incorporating a boron-containing D-mannopyranosidic unit form more stable cascade complexes with (S)-amino acid sodium or potassium salts than with the respective (R)-enantiomers. Complexes with sodium salts are more stable than the corresponding complexes with potassium salts as revealed by variable-temperature NMR measurements. Strong non-bonded interaction between the sugar unit and the α-substituents of the amino acids results in enantiomeric differentiation and destabilization of the complex. Complex formation is interpreted in terms of ion-pair inclusion by macrocyclic ring and nitrogen-boron interaction.