2017
Enantioselective Intermolecular C–O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst
Chinn AJ, Kim B, Kwon Y, Miller SJ. Enantioselective Intermolecular C–O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst. Journal Of The American Chemical Society 2017, 139: 18107-18114. PMID: 29116792, PMCID: PMC5738244, DOI: 10.1021/jacs.7b11197.Peer-Reviewed Original ResearchConceptsComplex molecular settingsO bond formationPeptide-based ligandsCross-coupling reactionsPhenolic hydroxyl groupsIntermolecular CuIntermolecular CChemoselective reactionTBu groupBond formationAppreciable selectivityReactive sitesPhenolic nucleophilesHydroxyl groupsSteric perturbationsMaximum enantioselectivitySecond reactive siteMolecular settingNucleophilesDesymmetrizationUncommon levelReactionSubstrateCatalystChemistryStereodynamic 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
2014
Spontaneous transfer of chirality in an atropisomerically enriched two-axis system
Barrett KT, Metrano AJ, Rablen PR, Miller SJ. Spontaneous transfer of chirality in an atropisomerically enriched two-axis system. Nature 2014, 509: 71-75. PMID: 24747399, PMCID: PMC4008667, DOI: 10.1038/nature13189.Peer-Reviewed Original Research