Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives
Alison L. Lambright, Yanyao Liu, Isaac A. Joyner, Kaitlyn M. Logan, M. Kevin Brown
Abstract
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.
Topics & Concepts
ChemistryAmideCyclopenteneCyclopentaneSteric effectsCatalysisCounterionFunctional groupCombinatorial chemistryOrganic chemistryIonPolymerOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis