A highly diastereoselective synthesis of deep molecular baskets

We describe a preparative method for directing Mizoroki-Heck cyclotrimerization of enantioenriched bromonorbornenes into molecular baskets having increasingly deeper and extendable aromatic cavities. Such diastereoselective cyclotrimerizations of the bromo-olefinic substrates resulted from prevalent β migratory insertions without the formation of palladacycle intermediate(s). The facile access to multigram quantity of a new series of basket-like hosts clears the way for creating novel supramolecular materials for storage, sequestration and catalysis. A novel synthetic method for obtaining multigram quantities of uniquely functionalized and deep molecular baskets is now available, clearing the way toward useful supramolecular materials.