2018
Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C−N Bond‐Forming Cross‐Coupling and Catalyst‐Controlled Atroposelective Cyclodehydration
Kwon Y, Chinn AJ, Kim B, Miller SJ. Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C−N Bond‐Forming Cross‐Coupling and Catalyst‐Controlled Atroposelective Cyclodehydration. Angewandte Chemie International Edition 2018, 57: 6251-6255. PMID: 29637680, PMCID: PMC5964046, DOI: 10.1002/anie.201802963.Peer-Reviewed Original ResearchConceptsAxis of chiralityCopper complexesChiral phosphoric acid catalystChiral copper complexesPhosphoric acid catalystStereogenic carbon centersMultiple stereoisomersCatalytic approachCatalytic reactionStereogenic elementsAcid catalystRemote desymmetrizationCatalyst controlAxial chiralityCarbon centerStereogenic centersCross couplingHigh diastereoselectivityPhosphoric acidCatalystChiralityStereoisomersCyclodehydrationStereogenicityReaction
2017
Stereodynamic Quinone–Hydroquinone Molecules That Enantiomerize at sp3‑Carbon via Redox-Interconversion
Kim B, Storch G, Banerjee G, Mercado BQ, Castillo-Lora J, Brudvig GW, Mayer JM, Miller SJ. Stereodynamic Quinone–Hydroquinone Molecules That Enantiomerize at sp3‑Carbon via Redox-Interconversion. Journal Of The American Chemical Society 2017, 139: 15239-15244. PMID: 28931280, PMCID: PMC5735348, DOI: 10.1021/jacs.7b09176.Peer-Reviewed Original ResearchConceptsRedox-active substituentsStereogenic carbon atomCarbon-bearing moleculesFunctional group migrationRedox interconversionChiral compoundsOrganic moleculesMolecular chiralityDifferent substituentsHydroquinone groupsSp3 carbonCarbon centerEnantiomerization pathwayMaterials scienceCarbon atomsChemical processesConstituent bondsGroup migrationMoleculesDeracemization processSubstituentsBondsChiralityCompoundsEnantiomerization