Preparation of a permethylated β-cyclodextrin chiral stationary phase by one-pot hydrosilylation and immobilization at the C2 position for chiral high-performance liquid chromatography.

A novel cyclodextrin intermediate, mono-2(A)-allylcarbamido-2(A)-deoxy-permethylated β-cyclodextrin, was synthesized by reacting allylamine and newly prepared mono-2(A)-azido-2(A)-deoxy-permethylated β-cyclodextrin by the Staudinger reaction and anchored onto porous silica beads by a one-pot hydrosilylation and immobilization procedure to afford a novel chiral stationary phase. This stationary phase acts as a new member of the previous chiral stationary phase series immobilized on the cyclodextrin C2 position. This stationary phase depicted enantiomeric separation abilities toward a series of bicyclic and tricyclic racemates under reversed-phase conditions. The resolutions for hesperetin and naringenin achieved on the current phase reached 3.91 and 1.11, respectively, much higher than the previous permethylated β-cyclodextrin with the linkage at the C6 position.