DIPHENYLETHANEDIAMINE (DPEDA) DERIVATIVES AS CHIRAL SELECTORS .4. A COMPARISON OF 3,5-DINITROBENZOYLATED (S,S)-DPEDA-DERIVED AND (S,R)-DPEDA-DERIVED CHIRAL STATIONARY PHASES WITH PIRKLES STANDARD (R)-PHENYLGLYCINE-DERIVED PHASE IN NORMAL-PHASE HPLC

Undecanoyl bound 3,5-dinitrobenzoyl-(S, R)-1, 2-diphenylethane-1,2-diamine [(1S,2R)-DNB-DPEDA] as chiral selector (SO) has been synthesized and used as a chiral stationary phase (CSP II) for normal-phase enantioselective HPLC. It is compared with the already published diastereomeric (1S, 2S)-DNB-DPEDA-derived CSP I and with the ''standard'' Pirkle DNB-(R)-phenylglycine-derived CSP III. Chromatographic data for about 100 racemic analytes reveal that CSP II is able to separate especially well enantiomers of derivatized aromatic carboxylic acids and analytes having a benzyl substituent bound at the chiral center. However, CSP I was found to be superior to CSP II and III in its general applicability and its ability to resolve enantiomers of heterocyclic drugs. (C) 1994 Wiley-Liss, Inc.