Diphenylethanediamine (DPEDA) as chiral selector IX: Self recognition of chiral selectors - Efficient HPLC-separation of the enantiomers of 3,5,-dinitrobenzoylated diphenylalkaneamides on the immobilized analogue

Chiral recognition between four 3,5-dinitrobenzoylated (DNB) diphenylalkane amine derived chiral stationary phases (CSPs) and their four racemic precur sors was studied via normal phase HPLC. In 13 cases successful enantiosepar ation (alpha = 1.08 - 5.08) of these pi-acceptor analytes could be achieved on the pi-acceptor CSPs. Characteristically, the stereochemistry of the DN B modified stereogenic center of the chiral selector and the more retained enantiomer of the corresponding precursor were identical. Simple model anal ytes gave very similar results. A double stacking model was suggested to co ordinate this behaviour with the Pirkle pi-donor-acceptor concept. Chiralit y 11:404-408, 1999. (C) 1999 Wiley-Liss, Inc.