The enantioselective synthesis of azahelicenes and S-shaped double azahelicenes has been achieved via the Au-catalyzed sequential intramolecular hydroarylation of alkynes. The use of excess AgOTf toward a Au(1) complex is crucial for this transformation. Interestingly, the circularly polarized luminescence activity of the S-shaped double azahelicenes was significantly higher than that of the azahelicenes.