A m-quaterphenyl probe for absolute configurational assignments of primary and secondary amines

We report a method for determining the absolute configurations of chiral amino alcohols, amino acid esters, and secondary amines through the combined use of a m -quaterphenyl probe 1 and theoretical calculations. The probe 1 is covalently attached to chiral amines to form conjugates that exhibit exciton-coupled circular dichroism (ECCD) in the m -quaterphenyl chromophores. The calculated ratios of the P and M conformers, obtained via DFT calculations, show a correlation with both the sign and intensity of the experimentally observed CD spectra.