Application of methyl itaconate–anthracene adducts (MIAs) in configuration assignment of chiral primary amines by means of 1H NMR

Abstract

Methyl itaconate–anthracene adducts (MIAs) were previously introduced as chiral derivatizing agents (CDAs) for the determination of chiral secondary alcohols. In this study, they were further employed with chiral primary amines to assign their absolute configuration. Each chiral amine compound was linked to the (R)- and (S)-MIAs through amidation to obtain diastereomeric amides in moderate yield. The modified Mosher's method was applied, where the difference in chemical shift (ΔδSR = δHS−MIA-amide – δHR−MIA-amide) values of each substituent of the chiral amine adducts was utilized to validate the capability of MIAs as CDAs. Finally, the proposed model was successfully achieved, and the MIAs were proven effective for the determination of the absolute configuration of chiral amines.