Introducing iteroselectivity

Today’s chemistry is a wide field of science with many different subfields that are all uniquely important for advancing our fundamental understanding of the properties of matter and how to manipulate it. Many of these subfields started to bloom after someone named them, thus allowing researchers to gather under a common banner. For instance, supramolecular interactions such as hydrogen bonds were studied long before Jean-Marie Lehn coined the term supramolecular chemistry in 1978,¹ yet the developments in this field have increased significantly since then to become one of the leading fields of chemistry.

As chemists working in the field of oligomeric macrocycles, we regularly came across reactions that selectively modified the same functional group on a given number of monomers. This is a peculiar type of selectivity that is not covered by the common selectivities in organic synthesis. Indeed, these reactions modify the same type of functional group so it is not a matter of chemoselectivity. The products differing by the number of reacted groups are not isomers, thus neither regioselectivity nor stereoselectivity would apply.