RETRACTED: Asymmetric remote C–H borylation of aliphatic amides and esters with a modular iridium catalyst
Ronald L. Reyes, Miyu Sato, Tomohiro Iwai, Kimichi Suzuki, Satoshi Maeda, Masaya Sawamura
Abstract
)-H bonds γ to the carbonyl group in aliphatic secondary and tertiary amides and esters. A chiral C-H activation catalyst was modularly assembled from an iridium center, a chiral monophosphite ligand, an achiral urea-pyridine receptor ligand, and pinacolatoboryl groups. Quantum chemical calculations support an enzyme-like structural cavity formed by the catalyst components, which bind the substrate through multiple noncovalent interactions. Versatile synthetic utility of the enantioenriched γ-borylcarboxylic acid derivatives was demonstrated.
Topics & Concepts
BorylationIridiumCatalysisAmideChemistryLigand (biochemistry)SubstituentPyridineSmall moleculeCombinatorial chemistryMoleculeEnantioselective synthesisReactivity (psychology)Hydrogen bondStereochemistryMedicinal chemistryOrganic chemistryArylPathologyBiochemistryAlternative medicineReceptorMedicineAlkylCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistryAsymmetric Hydrogenation and Catalysis