5-Amino-4-aryl-2,2-dimethyl-1,3-dioxans: application as chiral NMR shift reagents and derivatizing agents for acidic compounds

Abstract

The use of (4 S,5 S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxan (ADPD) and (4 R,5 R)-5-amino-(4′-biphenyl)-2,2-dimethyl-1,3-dioxan (ABDD) as chiral solvating agents (CSA) for the ee determination of compounds bearing an acidic proton by means of 1H NMR spectroscopy is demonstrated. In addition, based on the well known rigid conformation of these amines, ADPD and ABDD are suitable as chiral derivatizing agents (CDAs) in order to determine absolute configurations.