A chromatographic study on the exceptional chiral recognition of 2-(benzylsulfinyl)benzamide by animmobilized-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate)

In previous studies, Okamoto et al. described the results of the exceptionally large chiral recognitionof 2-(benzylsulfinyl)benzamide onto a coated-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate). As a continuation and deepening of those studies, here the sulfoxide and asmall set of its structural analogues were analyzed on the commercially available Chiralpak IC-3 chiralstationary phase based upon the same polysaccharide derivative as the chiral selector but immobilizedonto silica support.The chromatographic results obtained using different mobile phases consisting of pure methanol,ethanol and 2-propanol or binary mixtures n-hexane-2-propanol, which are prohibited with the pro-genitor coated-type chromatographic support, permitted to identify the NH2of the amide group as thekey structural element of the (S)-enantiomer of 2-(benzylsulfinyl)benzamide for obtaining a very highaffinity for the IC-3 chiral stationary phase.