Mechanically interlocked molecules can be chiral if each of the rings has no bilateral symmetry. Although chiral catenanes have been isolated from racemic mixtures via chromatographic techniques, these optically active molecules have not been directly synthesized until now. In this issue of Chem, Goldup and co-workers describe an auxiliary approach for the stereoselective synthesis of the topological enantiomers of chiral [2]catenanes. This methodology enables exploration of the potential applications of these chiral molecules in areas such as medicine and materials science.