Enantioselective fluorescent sensor for amino acid derivatives based on BINOL bearing hexahydropyrrolo[1,2-c]imidazol-1-one units

A chiral fluorescent sensor (Ra,S,l)-3 incorporating (R)-BINOL and l-prolinamide is found efficient in enantioselective recognition of N-Cbz-protected phenylglycine. It is observed that one enantiomer of N-Cbz-protected phenylglycine can obviously increase the fluorescence intensity of (Ra,S,l)-3, while the other enantiomer does not cause much fluorescence enhancement. Such highly enantioselective response makes the sensor (Ra,S,l)-3 useful for the enantioselective fluorescence recognition of other N-Cbz-protected amino acids.