Mechanically interlocked molecules are constituted of one or more molecular fragments held together or in a particular conformation by one or more mechanical bonds. These are enforced primarily by steric repulsion and allow the formation of knotted and chained architectures. The resulting unique translational and conformational properties are unlike those of any other chemical bond. Nevertheless, establishing a mechanical bond is a challenging endeavour and only a handful of synthetic methods have proven effective. Prior to the present work, our group investigated the use of covalent templates to force the “backfolding” macrocyclization of linear molecular fragments. Several inverted-spiro bismacrocycles could be isolated possessing a mechanical bond. Although effective in establishing the correct interlocked conformation, the templates proved impossible to cleave, thus never fully liberating the desired interlocked final product. In this work, the unexpected stability of the template linkages was investigated and successfully tackled, leading to the first [2]catenane obtained by backfolding macrocyclization using covalent templating. The approach was further improved with the introduction of an aminoacid template which required milder conditions to liberate the final interlocked species, as well as a lower degree of symmetry, giving rise to observable mechanical stereoisomers. This second approach lead to both a [2]catenane and a [2]rotaxane via a common late stage intermediate. A simpler terephthalate template was also explored in the preparation of a large number of rotaxanes by joining several different building blocks into a number of combinations. Mechanical chirality could also be introduced in this system.