Efficient high-performance liquid chromatographic enantioseparation of five-membered aryl-substituted lactones and cyclic carbamates on a ( R, R)-diaminodihydroethanoanthracene-derived chiral stationary phase

Abstract

The synthesis and valuation of a new bis-3,5-dinitrobenzoylated trans-(−)-(11 R,12 R)-(−)-diamino-9,10-dihydro-9,10- ethanoanthracene (DADEA)-based chiral stationary phase are described. In comparison to the well established structurally related diaminocylohexane (DACH)-derived CSP, this conformationally more rigid selector exhibits significantly improved enantiodiscrimination capabilities for five-membered cyclic esters and carbamates with an aromatic substituent at the carbon next to the ring oxygen. Differences in the enantiorecognition behaviour between the new selector and DACH and diphenylethanediamine-derived analogues are discussed. The chromatographic results obtained for oxazolidinones of important β-blockers, phthalides and glycine-derived oxazolidine-5-ones, potentially useful as chiral synthons, are reported and discussed.