Abstract: High performance liquid chromatography (HPLC) is a commonly used Chiral separation method for the resolution of chiral compounds. The key to chromatographic resolution lies in exploring new and efficient stationary phases. Chiral porous organic cage is a new kind of pure organic porous crystal material. In this study, a chiral porous pentyl cage with homochiral structure was synthesized. The chiral porous pentyl cage was coated on silica gel to prepare a coated HPLC chiral stationary phase. The chiral recognition ability of the chiral stationary phase for chiral compounds was studied using n-hexane/isopropanol as mobile phase. The results show that the chiral column exhibited good recognition ability toward some chiral compounds.