Supramolecular Control over Organic Reactivity
Abstract: Chemists strive to exert complete control over the selectivity (chemo-, regio-, diastereo-, enantio-) of organic reactions. This is usually done by relying on the inherent reactivity of the functional groups featured in the substrate, coupled with the nature of their interactions with a reagent or a catalyst. However, traditional methods often fail when tested on molecules featuring several similarly reactive sites. In such cases, enzymes can overcome challenging selectivity issues and distinguish between such sites by interacting with the substrate as a whole, rather than “seeing” only isolated functional groups.
Nature’s success in this area has inspired the development of artificial supramolecular hosts, which can accommodate small molecules within their cavities. The chemical behavior of the encapsulated substrates dramatically differs from their reactivity in solution, uncovering fundamentally new transformations and mechanisms. This seminar will survey examples of such cases and hopefully illustrate the potential of this emerging idea.