2024
Catalyst–Substrate Pairings for Carbocyclic and Heterocyclic Systems in Atroposelective Quinazolinone Synthesis
Guo M, Miller S. Catalyst–Substrate Pairings for Carbocyclic and Heterocyclic Systems in Atroposelective Quinazolinone Synthesis. ACS Catalysis 2024, 17226-17232. DOI: 10.1021/acscatal.4c05014.Peer-Reviewed Original ResearchChiral phosphoric acidPositive nonlinear effectNon-covalent interactionsQuinazolinone synthesisHeterocyclic systemsCatalyst scaffoldHigh enantioselectivityNitrogen heteroatomsEnantiomeric ratioCatalystReaction developmentCatalytic scaffoldMechanistic studiesEnantioselectivityPhosphoric acidSubstrateCarbocyclesCyclocondensationHeterocyclesHeteroatomsScaffoldsReactionSynthesisReactivityYieldCatalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides
Huth S, Tampellini N, Guerrero M, Miller S. Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides. Organic Letters 2024, 26: 6872-6877. PMID: 39102356, PMCID: PMC11329351, DOI: 10.1021/acs.orglett.4c02452.Peer-Reviewed Original ResearchConceptsEnantioselective oxidation of sulfidesModel of transition stateLevels of enantioinductionOxidation of sulfidesChiral sulfoxidesPeptide catalystsTransition stateEnantioselective sulfoxidationAspartic acid-containing peptidesSulfoxideThioethersEnantioinductionCatalystMoietySubstrateHydrogenSulfideExperimental evidence
2018
Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones
Shugrue C, Featherston AL, Lackner RM, Lin A, Miller SJ. Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones. The Journal Of Organic Chemistry 2018, 83: 4491-4504. PMID: 29547285, PMCID: PMC5963540, DOI: 10.1021/acs.joc.8b00207.Peer-Reviewed Original ResearchConceptsReductive aminationNumerous reactive sitesPeptide catalystsParallel kinetic resolutionDFT calculationsNMR studiesReactive sitesDivergent selectivitySecondary interactionsNatural productsKinetic resolutionCatalystAminationDivergent stereoselectivitiesCatalyzed Reductive AminationPeptide sequencesSelectivityComplex substratesSubstrateDiastereoselectivityStereoselectivityProductsReactivityPhosphopeptidesPhosphothreonine
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 levelReactionSubstrateCatalystChemistry
2016
Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
Kim B, Chinn AJ, Fandrick DR, Senanayake CH, Singer RA, Miller SJ. Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling. Journal Of The American Chemical Society 2016, 138: 7939-7945. PMID: 27254785, PMCID: PMC5127171, DOI: 10.1021/jacs.6b03444.Peer-Reviewed Original Research
2015
Site-Selective Reactions with Peptide-Based Catalysts
Giuliano MW, Miller SJ. Site-Selective Reactions with Peptide-Based Catalysts. 2015, 372: 157-201. PMID: 26307403, DOI: 10.1007/128_2015_653.Peer-Reviewed Original ResearchPhosphothreonine as a Catalytic Residue in Peptide‐Mediated Asymmetric Transfer Hydrogenations of 8‐Aminoquinolines
Shugrue CR, Miller SJ. Phosphothreonine as a Catalytic Residue in Peptide‐Mediated Asymmetric Transfer Hydrogenations of 8‐Aminoquinolines. Angewandte Chemie International Edition 2015, 54: 11173-11176. PMID: 26246129, PMCID: PMC4628550, DOI: 10.1002/anie.201505898.Peer-Reviewed Original ResearchConceptsTransfer hydrogenationChiral phosphoric acid catalystHydrogen bonding interactionsPhosphoric acid catalystAsymmetric transfer hydrogenationEnantioselective transfer hydrogenationAsymmetric catalystsAcid catalystStrong complexationNMR studiesSubstrate classesCatalystHydrogenationNew classCatalytic residuesPeptidesComplexationEnantioselectivityQuinolinePhosphopeptidesSubstrateResidues
2012
Catalytic Site-Selective Thiocarbonylations and Deoxygenations of Vancomycin Reveal Hydroxyl-Dependent Conformational Effects
Fowler BS, Laemmerhold KM, Miller SJ. Catalytic Site-Selective Thiocarbonylations and Deoxygenations of Vancomycin Reveal Hydroxyl-Dependent Conformational Effects. Journal Of The American Chemical Society 2012, 134: 9755-9761. PMID: 22621706, PMCID: PMC3374881, DOI: 10.1021/ja302692j.Peer-Reviewed Original ResearchConceptsPeptide-based catalystsForm of vancomycinNew compoundsVancomycin derivativesRational designConformational consequencesCatalystConformational effectsNew analoguesSelectivity profileBiological activityThiocarbonylationDeoxygenationNative structureStructural roleHydroxylCompoundsDerivativesAnaloguesSubstrateStructure