Conférence présentée par le professeur Ilan Marek, du Technion - Israel Institute of Technology
Combining functionalization at a distant position from a reactive site with the creation of several consecutive stereogenic centers, including the formation of one or more quaternary carbon stereocenters, in acyclic system represents a pinnacle in organic synthesis. Here we report the regioselective transformation of terminal olefins as a distant trigger for the ring-opening of cyclopropanes. This metal-catalyzed unfolding of the strained cycle, driving force of the chain-walking process, remarkably proved its efficiency and versatility, as the reaction proceeded regardless of the molecular distance between the initiation (double bond) and termination sites. Moreover, employing stereodefined polysubstituted cyclopropane vaults allowed to access sophisticated stereoenriched acyclic scaffolds in good yields.