To overcome this synthetic bottleneck, new stereoselective methods are required. The first approach to this challenging goal was reported by Takata, Okamoto and co-workers in 2007 using a catalytic enantioselective kinetic resolution strategy; the acylation of a dynamic mixture of enantiomeric pseudorotaxanes gave rise to a small (~4% ee) but measurable stereoselectivity. In 2020, Leigh and co-workers reported the synthesis of a mechanically planar chiral rotaxane in 50% ee using a substrate-controlled strategy in which a chiral leaving group was used to influence the configuration of the mechanical bond. Kawabata and coworkers have reported the catalytic enantioselective kinetic resolution of a mechanically planar chiral rotaxane (>99% ee of unreacted starting material, 29% isolated yield). Most recently, Zhu, Tian and co-workers reported the catalytic enantioselective desymmetrisation of rotaxanes containing a bilaterally symmetric macrocycle in up to 93% ee. Our approach has been to focus on methods equivalent to chiral auxiliary strategies in covalent synthesis. In 2018, building on a previously reported non-stereoselective approach, 10 we disclosed the active template 11 Cu-mediated alkyne-azide cycloaddition (AT-CuAAC) synthesis of mechanically planar chiral rotaxanes in up to 96% ee without separation of the intermediate diastereomers. This approach was then extended to a chiral interlocking auxiliary strategy. We subsequently demonstrated an auxiliary approach to analogous chiral catenanes, although in this case a lower diastereoselectivity (dr = 2 : 1) was observed in the mechanical bond forming step which necessitated the separation of diastereomers prior to auxiliary cleavage. We have since extended our methodology to a highly stereoselective synthesis of a mechanically chiral catenane (82% ee) and a molecule containing an analogous co-conformational stereogenic unit (87% ee). At this point we note that, although such chiral catenanes have typically been referred to simply as "topologically" chiral, this label clearly makes no sense in the context of co-conformational stereochemistry. Furthermore, we have recently demonstrated the synthesis of a catenane with the same stereogenic unit but whose stereochemistry is Euclidean. For these reasons we have tentatively suggested that these stereogenic units of rotaxanes and catenanes be united under the single term "mechanically planar chiral"; we shall use this term throughout. Most recently, we have extended our auxiliary approach to mechanically axially chiral catenanes and, in the process, identified an overlooked mechanically axial chiral rotaxane stereogenic unit. Although our published AT-CuAAC auxiliary strategies for the synthesis of mechanically planar chiral rotaxanes and catenanes rely on the same underlying concept, they use very different chiral building blocks because, to date, the chiral auxiliary has been included in the half-axle or pre-macrocycle component respectively, rather than the oriented bipyridine macrocycle that mediates the AT-CuAAC reaction, and which is common to both syntheses. Here we demonstrate a unified approach to these related mechanical stereogenic units by including an amino acid-derived chiral auxiliary in a readily available, oriented bipyridine macrocycle. This very simple modification is both extremely efficient and extremely flexible, as we demonstrate below through the synthesis of mechanically planar chiral rotaxanes and catenanes in excellent stereopurity. To emphasize this point further, we applied this approach to the iterative synthesis of all three stereoisomers of a co-conformationally mechanically planar chiral [3]rotaxane.