2016
Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity
Alford JS, Abascal NC, Shugrue CR, Colvin SM, Romney DK, Miller SJ. Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity. ACS Central Science 2016, 2: 733-739. PMID: 27800556, PMCID: PMC5084076, DOI: 10.1021/acscentsci.6b00237.Peer-Reviewed Original ResearchBaeyer-Villiger oxidationAlkene epoxidationSmall-molecule catalystsModes of reactivityOrthogonal chemical reactivityFunctional group selectivityCarboxylic acid groupsCatalytic functional groupsLate-stage diversificationDifferent chemical reactionsActive site carboxylatesMacromolecular architecturesPolyfunctional moleculesChemical reactivityChemical selectivityElectrophilic oxidantSelective reactionGroup selectivityAmide bondAcid groupsFunctional groupsActive siteCatalytic mechanismChemical reactionsCatalystSolution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer–Villiger Oxidation
Abascal NC, Miller SJ. Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer–Villiger Oxidation. Organic Letters 2016, 18: 4646-4649. PMID: 27588823, PMCID: PMC5130343, DOI: 10.1021/acs.orglett.6b02282.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsStereoselective Baeyer–Villiger oxidationsCatalytic reactionStereoselective catalystsEffect of additivesSolution conformationCatalystMolecular associationSubstrate-specific interactionsUnique structureSolution structureOxidationStructural analysisAdvantageous featuresSelectivityExperimental observationsPeptidesConformationStructureAdditivesReaction
2015
A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer–Villiger Oxidation
Giuliano MW, Lin C, Romney DK, Miller SJ, Anslyn EV. A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer–Villiger Oxidation. Advanced Synthesis & Catalysis 2015, 357: 2301-2309. PMID: 26543444, PMCID: PMC4629862, DOI: 10.1002/adsc.201500230.Peer-Reviewed Original ResearchAsymmetric Baeyer–Villiger oxidationBaeyer-Villiger oxidationSolution-phase reactionsBaeyer-Villiger monooxygenasesPeptide catalystsCatalyst discoveryChiroptical studiesSpeed of analysisCatalyst performanceFocused libraryLactone productsAsymmetric inductionAbsolute configurationCombinatorial screeningOxidationCatalystDistinct parallelsProductsReactionHPLCAlcoholMonooxygenases
2014
Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
Romney DK, Colvin SM, Miller SJ. Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones. Journal Of The American Chemical Society 2014, 136: 14019-14022. PMID: 25250713, PMCID: PMC4195385, DOI: 10.1021/ja508757g.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsHydrogen bonding interactionsTypes of selectivityParallel kinetic resolutionCatalyst controlFunctionalized KetonesCyclic ketonesFunctional groupsNatural productsComplex moleculesKinetic resolutionAsymmetric processEnantioselectivityRegioKetonesOxidationBroad utilityCatalystCatalysisSelectivityAmidesSynthesisMoleculesProducts