It is wildly known that racemic propranolol has dramatically side effects to cardiovascular patients. Thus, it's important to develop a new approach to synthesize the chiral propranolol. In present study, a novel synthetic route to chiral propranolol was carried out, using natural and cheap D-mannitol as starting material. The structures of all the synthesised compounds were confirmed by their IR, 1H NMR spectral data, and the results of HPLC showed that enantioselectivities up to 99% ee and chemical yields up to 97% have been obtained.