Atropisomerism is a fundamental property of molecules featuring a hindered rotation around a chemical bond. If six-membered ring biaryl or heterobiaryl atropisomers are the most popular ones, the focus of this feature article will be put on less common and more challenging five-membered ring containing atropisomers displaying either a stereogenic C–N or C–C bond. After an historical background, a description of the latest flourishing enantioselective strategies for the construction of this attractive family of atropisomers will be presented.