Novel chiral imidazole cyclophane receptors: synthesis and enantioselective recognition for amino acid derivatives

Abstract

Novel chiral imidazole cyclophane receptors were synthesized by highly selective N-alkylation of the imadazolyl 1N-position of the bridged histidine diester 2 with the dibromide in the presence of NaH; these receptors exhibit good chiral recognition toward the enantiomers of L- and D-amino acid derivatives (up to KD/KL = 3.52, delta delta G0 = -3.11 kJ mol-1) in CHCl3 at 25.0 degrees C.