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Diphenylethanediamine (DPEDA) derivatives as chiral selectors: IV. A comparison of 3,5‐dinitrobenzoylated (S,S)‐ and (S,R)‐DPEDA‐derived chiral stationary phases with Pirkle's standard (R)‐phenylglycine‐derived phase in normal phase HPLC

1994; Wiley; Volume: 6; Issue: 2 Linguagem: Inglês

10.1002/chir.530060212

1520-636X

Norbert M. Maier, Georg Uray, Oliver P. Kleidernigg, Wolfgang Lindner,

Molecular spectroscopy and chirality

Abstract 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. © 1994 Wiley‐Liss, Inc.