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 levelReactionSubstrateCatalystChemistrySite- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids
Key HM, Miller SJ. Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids. Journal Of The American Chemical Society 2017, 139: 15460-15466. PMID: 28975793, PMCID: PMC5736372, DOI: 10.1021/jacs.7b08775.Peer-Reviewed Original ResearchConceptsComplex moleculesSite-selective catalysisComplex molecular settingsComplex natural productsSite-selective modificationPotassium saltNew analoguesApplication of RhFunctional group toleranceEnantioselective catalysisSelective functionalizationCatalyst systemAnalogous reactionStereoselective functionalizationEnantioselective synthesisGroup toleranceNatural productsActive moleculesPotent antibacterial propertiesDehydroalanine residuesBiological testingAmino estersHigh stereoselectivityAntibacterial propertiesMolecular setting