Pd(0)-catalyzed amination in the synthesis of chiral derivatives of BINAM and their evaluation as fluorescent enantioselective detectors

Abstract

A mini-review covers recent successes in the synthesis of (S)-1,1'-binaphthyl-2,2'-diamine (BINAM) using Pd(0)-catalyzed amination reactions. As a result, versatile compounds with C2-chiral backbone were synthesized, among them are derivatives bearing additional chiral amino and fluorophore groups like dansyl amide, 7-methoxycoumarin, 6-aminoquinoline, different macrocyclic compounds with oxadiamine and polyamine linkers were obtained as well. BINAM derivatives of various structures were evaluated as fluorescent enantioselective detectors for a series of model amino alcohols. Many of them were shown to be efficient in sensing certain enantiomers of the amino alcohols by selective changes in the emission in the presence of these analytes. Small changes in the structure of the BINAM derivatives lead to serious difference in the recognition ability of the compounds under investigation.