Separation of atropisomeric 1,4,5,6-tetrahydropyrimidinium salts by chiral HPLC and determination of their enantiomerization barriers

Chiral HPLC separation of a series of novel atropisomeric quaternary (1) and ternary (2) 1,2-disubstituted 1,4,5,6-tetrahydropyrimidinium salts bearing disymmetric aryl groups in positions 1 and/or 2 is described. A screening of different polysaccharide stationary phases (OD-R, OJ-R and AD-RH) and chromatographic conditions allowed for partial or baseline resolution of 16 over 26 compounds. When a semi-preparative separation was achieved, the corresponding enantiomerization barriers were determined employing the off-column method. The experimental data were compared inter se in order to establish the factors influencing the magnitude of the barriers and with those corresponding to the parent amidines.