Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives

A method
for amide-directed Ni-catalyzed diastereoselective arylboration
of cyclopentenes is disclosed. The reaction allows for the synthesis
of sterically congested cyclopentane scaffolds that contain an easily
derivatized boronic ester and amide functional handles. The nature
of the amide directing group and its influence on the reaction outcome
are investigated and ultimately reflect a predictably selective reaction
based on the solvent and base counterion.