The enantiomeric chiral separation of propranolol and several aryloxyaminopropan-2-ol analogs is studied using two cellulose-type chiral stationary phases (CSPs) namely Chiralcel OF and Chiralcel OC and one amylose type chiral stationary phase (CSP), Chiralpak AD. The results showed base-line separation for all the compounds studied using amylose tris (3,5-dimethylphenyl carbamate) known as Chiralpak AD in comparison to the cellulose tris (4-chlorophenylcarbamate) known as Chiralcel OF which showed a significant decrease in the selectivities for most of the compounds, while partial or no separation were obtained using cellulose tris (phenylcarbamate) known as Chiralcel OC.