Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush-type chiral stationary phases.
The chiral discrimination ability of two recently prepared chiral stationary phases (CSP 1 and CSP 2), based on a leucine derived chiral selector, was tested for the enantiomers of dihydropyrimidone (DHPM) derivatives and compared with the commercially available Hyun-leucine CSP 3 and classical Pirkle-leucine CSP 4. By combining all of these CSPs, the enantiomers of all DHPM derivatives used in this study can be properly resolved. Particularly good enantioresolutions were achieved for thioureide derivatives, such as Monastrol. The results presented show that sulfur-aromatic interactions are meritorious for these very good separations.
Forjan
Davorka Moslavac
DM
Laboratory for Stereoselective Catalysis and Biocatalysis, Ruder Bosković Institute, Bijeniccka cesta 54, Zagreb, Croatia.
Gazić
Ivana
I
Vinković
Vladimir
V
D002623:Chemistry Techniques, Analytical / Q000379:methods; D002845:Chromatography / Q000379:methods; D002853:Chromatography, Liquid / Q000379:methods*; D008956:Models, Chemical; D008968:Molecular Conformation; D011743:Pyrimidines / Q000737:chemistry; D011744:Pyrimidinones / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D013871:Thiones / Q000737:chemistry; D013997:Time Factors
D011743:Pyrimidines; D011744:Pyrimidinones; D013871:Thiones; C400223:monastrol; D013455:Sulfur