Evaluation of aromatic-derivatized cyclofructans 6 and 7 as HPLC chiral selectors

Abstract

The two best aromatic-functionalized cyclofructan chiral stationary phases, R-naphthylethyl-carbamate cyclofructan 6 (RN-CF6) and dimethylphenyl-carbamate cyclofructan 7 (DMP-CF7), were synthesized and evaluated by injecting various classes of chiral analytes. They provided enantioselectivity toward a broad range of compounds, including chiral acids, amines, metal complexes, and neutral compounds. It is interesting that they exhibited complementary selectivities and the combination of two columns provided enantiomeric separations for 43% of the test analytes. These extensive chromatographic results provided useful information about method development of specific analytes, and also gave some insight as to the enantioseparation mechanism.

Preparation and Evaluation of HPLC Chiral Stationary Phases Based on Cationic/Basic Derivatives of Cyclofructan 6

“…[5–7] Therefore, basic/cationic substitution groups on cyclofructan 6 (CF6), including amine and aromatic groups, such as imidazole, benzimidazole, pyridine, aliphatic and aromatic amines, were tested. Chiral recognition of these stationary phases may be attributed to the presence of hydrogen bonding sites, π-π interactions, electrostatic interactions (for ionizable analytes) and/or steric hindrance which are mainly provided by the substitutions on the CF6.…”

Recent advances in the direct and indirect liquid chromatographic enantioseparation of amino acids and related compounds: A review

“…Two aromatic-functionalized cyclofructan CSPs, Rnaphthylethyl-carbamate cyclofructan6 (RN-CF6) and dimethylphenyl-carbamate cyclofructan7 (DMP-CF7), were synthesized and evaluated by investigating various classes of chiral analytes [100] (Table 2). They provided enantioselectivity toward a broad range of compounds, including chiral acids, amines, metal complexes, and neutral compounds.…”

Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases

“…ENREF 9 In this study, three functionalized cyclofructan CSP's were evaluated for use as HPLC CSP's. The first, the LARIHC CF6-P (isopropylcarbamate derivatized cyclofructan-6) has shown exceptional selectivity for racemates with a primary amine moiety[30] while the LARIHC CF6-RN (R-napthyethylcarbamate derivatized cyclofructan-6) and LARIHC CF7-DMP (dimethyphenylcarbamate derivatized cyclofructan-7) CSP's have shown broad selectivity and applicability for a variety of classes of molecules[31 -35]. …”