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 evidenceFe/Thiol Cooperative Hydrogen Atom Transfer Olefin Hydrogenation: Mechanistic Insights That Inform Enantioselective Catalysis
Buzsaki S, Mason S, Kattamuri P, Serviano J, Rodriguez D, Wilson C, Hood D, Ellefsen J, Lu Y, Kan J, West J, Miller S, Holland P. Fe/Thiol Cooperative Hydrogen Atom Transfer Olefin Hydrogenation: Mechanistic Insights That Inform Enantioselective Catalysis. Journal Of The American Chemical Society 2024, 146: 17296-17310. PMID: 38875703, PMCID: PMC11209773, DOI: 10.1021/jacs.4c04047.Peer-Reviewed Original ResearchMetal-catalyzed hydrogen atom transferChiral thiolsAsymmetric hydrogenationSynthesis of complex moleculesMinimally functionalized olefinsSelectivity-determining stepTransition metal catalysisHydrogen atom transferOff-cycle speciesH-atom donorsTransfer of hydrideAsymmetric inductionElectron-richAtom transferMetal catalysisEnantioselective reductionThiol catalystMetal catalystsAlkyl radicalsElectron-neutralIron speciesOlefinsTraditional hydrogenationEnantiomeric ratioRadical catalysisβ‑Amino Acids Reduce Ternary Complex Stability and Alter the Translation Elongation Mechanism
Cruz-Navarrete F, Griffin W, Chan Y, Martin M, Alejo J, Brady R, Natchiar S, Knudson I, Altman R, Schepartz A, Miller S, Blanchard S. β‑Amino Acids Reduce Ternary Complex Stability and Alter the Translation Elongation Mechanism. ACS Central Science 2024, 10: 1262-1275. PMID: 38947208, PMCID: PMC11212133, DOI: 10.1021/acscentsci.4c00314.Peer-Reviewed Original ResearchNon-natural amino acidsComplex stabilityTernary complex stabilityTemplate synthesisDetection limitEnergy transfer measurementsTernary complex formationComplex formationSingle-molecule fluorescence resonance energy transfer measurementsIn vitro detection limitTernary complexFluorescence resonance energy transfer measurementsAmino acidsMechanism of protein synthesisResonance energy transfer measurementsSynthesis of proteinsRate of translocationMRNA decodingElongation substratesStabilityElongation factorIsomersRibosome utilizationAminoacyl-tRNAStereoisomersThank You, Steve Ritter!
Dehnen S, Chirik P, Kozlowski M, Miller S, Rossen K. Thank You, Steve Ritter! The Journal Of Organic Chemistry 2024, 89: 7353-7354. PMID: 38801183, DOI: 10.1021/acs.joc.4c01178.Peer-Reviewed Original ResearchThank You, Steve Ritter!
Dehnen S, Chirik P, Kozlowski M, Miller S, Rossen K. Thank You, Steve Ritter! Organic Letters 2024, 26: 4581-4582. PMID: 38801189, DOI: 10.1021/acs.orglett.4c01749.Peer-Reviewed Original ResearchThank You, Steve Ritter!
Dehnen S, Chirik P, Kozlowski M, Miller S, Rossen K. Thank You, Steve Ritter! Inorganic Chemistry 2024, 63: 10453-10454. PMID: 38801179, DOI: 10.1021/acs.inorgchem.4c01965.Peer-Reviewed Original ResearchScaffold‐Oriented Asymmetric Catalysis: Conformational Modulation of Transition State Multivalency during a Catalyst‐Controlled Assembly of a Pharmaceutically Relevant Atropisomer
Tampellini N, Mercado B, Miller S. Scaffold‐Oriented Asymmetric Catalysis: Conformational Modulation of Transition State Multivalency during a Catalyst‐Controlled Assembly of a Pharmaceutically Relevant Atropisomer. Chemistry - A European Journal 2024, 30: e202401109. PMID: 38507249, PMCID: PMC11132932, DOI: 10.1002/chem.202401109.Peer-Reviewed Original ResearchHydrogen bond donorAtroposelective synthesisAsymmetric catalysisGuanidine catalystCatalyst controlChiral axisBond donorNoncovalent interactionsConformational modulationCatalystFolded stateN-capAtroposelectivityAtropisomersSuperbasesPhenylCatalysisQuinazolinedionesMultivalencyBTK inhibitorsMechanistic frameworkStructureEnantioselective Sulfonimidamide Acylation via a Cinchona Alkaloid-Catalyzed Desymmetrization: Scope, Data Science, and Mechanistic Investigation
Haas B, Lim N, Jermaks J, Gaster E, Guo M, Malig T, Werth J, Zhang H, Toste F, Gosselin F, Miller S, Sigman M. Enantioselective Sulfonimidamide Acylation via a Cinchona Alkaloid-Catalyzed Desymmetrization: Scope, Data Science, and Mechanistic Investigation. Journal Of The American Chemical Society 2024, 146: 8536-8546. PMID: 38480482, PMCID: PMC10990064, DOI: 10.1021/jacs.4c00374.Peer-Reviewed Original ResearchConceptsDensity functional theoryStructure-activity relationshipBis-acylationExcellent yieldsAsymmetric acylationTetrahedral intermediateSynthetic chemistryFunctional theoryMechanistic investigationsReaction kineticsMechanistic studiesSulfonimidamidesDesymmetrizationEnantioselectivityStructural studiesCatalystAcylPharmacophoreCinchonaIntermediateReactionChemistryKineticsYield
2023
Introduction: Remote and Late Stage Functionalization
Miller S, Ritter T. Introduction: Remote and Late Stage Functionalization. Chemical Reviews 2023, 123: 13867-13868. PMID: 38148744, DOI: 10.1021/acs.chemrev.3c00800.Peer-Reviewed Original ResearchData Science-Enabled Palladium-Catalyzed Enantioselective Aryl-Carbonylation of Sulfonimidamides
van Dijk L, Haas B, Lim N, Clagg K, Dotson J, Treacy S, Piechowicz K, Roytman V, Zhang H, Toste F, Miller S, Gosselin F, Sigman M. Data Science-Enabled Palladium-Catalyzed Enantioselective Aryl-Carbonylation of Sulfonimidamides. Journal Of The American Chemical Society 2023, 145: 20959-20967. PMID: 37656964, DOI: 10.1021/jacs.3c06674.Peer-Reviewed Original ResearchCross-coupling methodsHeteroaryl iodidesLigand descriptorsExcellent yieldsCoupling partnersChemical spaceMedicinal chemistrySulfonimidamidesAgrochemical discoveryVirtual libraryReaction optimizationOptimal conditionsEfficient strategyHeteroarylScience techniquesEnantioselectivityArylCatalystIodideReactionChemistryData science techniquesYieldDescriptorsDiverse setNew Guidelines for Presenting Electrochemical Data in All ACS Journals
Minteer S, Chen J, Lin S, Crudden C, Dehnen S, Kamat P, Kozlowski M, Masson G, Miller S. New Guidelines for Presenting Electrochemical Data in All ACS Journals. ACS Catalysis 2023, 13: 4468-4469. DOI: 10.1021/acscatal.3c00995.Peer-Reviewed Original ResearchNew Guidelines for Presenting Electrochemical Data in All ACS Journals
Minteer S, Chen J, Lin S, Crudden C, Dehnen S, Kamat P, Kozlowski M, Masson G, Miller S. New Guidelines for Presenting Electrochemical Data in All ACS Journals. Organic Letters 2023, 25: 1999-2000. PMID: 36939864, DOI: 10.1021/acs.orglett.3c00686.Peer-Reviewed Original ResearchNew Guidelines for Presenting Electrochemical Data in All ACS Journals
Minteer S, Chen J, Lin S, Crudden C, Dehnen S, Kamat P, Kozlowski M, Masson G, Miller S. New Guidelines for Presenting Electrochemical Data in All ACS Journals. ACS Measurement Science Au 2023, 3: 82-83. PMID: 37090260, PMCID: PMC10120028, DOI: 10.1021/acsmeasuresciau.3c00008.Peer-Reviewed Original ResearchNew Guidelines for Presenting Electrochemical Data in All ACS Journals
Minteer S, Chen J, Lin S, Crudden C, Dehnen S, Kamat P, Kozlowski M, Masson G, Miller S. New Guidelines for Presenting Electrochemical Data in All ACS Journals. ACS Energy Letters 2023, 8: 1793-1794. DOI: 10.1021/acsenergylett.3c00470.Peer-Reviewed Original ResearchNew Guidelines for Presenting Electrochemical Data in All ACS Journals
Minteer S, Chen J, Lin S, Crudden C, Dehnen S, Kamat P, Kozlowski M, Masson G, Miller S. New Guidelines for Presenting Electrochemical Data in All ACS Journals. Inorganic Chemistry 2023, 62: 5047-5048. PMID: 36939846, DOI: 10.1021/acs.inorgchem.3c00704.Peer-Reviewed Original ResearchNew Guidelines for Presenting Electrochemical Data in All ACS Journals
Minteer S, Chen J, Lin S, Crudden C, Dehnen S, Kamat P, Kozlowski M, Masson G, Miller S. New Guidelines for Presenting Electrochemical Data in All ACS Journals. The Journal Of Organic Chemistry 2023, 88: 4036-4037. PMID: 36939845, DOI: 10.1021/acs.joc.3c00476.Peer-Reviewed Original ResearchNew Guidelines for Presenting Electrochemical Data in All ACS Journals
Minteer S, Chen J, Lin S, Crudden C, Dehnen S, Kamat P, Kozlowski M, Masson G, Miller S. New Guidelines for Presenting Electrochemical Data in All ACS Journals. ACS Organic & Inorganic Au 2023, 3: 72-73. PMID: 37035282, PMCID: PMC10080720, DOI: 10.1021/acsorginorgau.3c00009.Peer-Reviewed Original Research
2021
Green Chemistry: A Framework for a Sustainable Future
Ganesh K, Zhang D, Miller S, Rossen K, Chirik P, Kozlowski M, Zimmerman J, Brooks B, Savage P, Allen D, Voutchkova-Kostal A. Green Chemistry: A Framework for a Sustainable Future. Industrial & Engineering Chemistry Research 2021, 60: 8964-8968. DOI: 10.1021/acs.iecr.1c02213.Peer-Reviewed Original ResearchGreen Chemistry: A Framework for a Sustainable Future
Ganesh K, Zhang D, Miller S, Rossen K, Chirik P, Kozlowski M, Zimmerman J, Brooks B, Savage P, Allen D, Voutchkova-Kostal A. Green Chemistry: A Framework for a Sustainable Future. ACS Sustainable Chemistry & Engineering 2021, 9: 8336-8340. DOI: 10.1021/acssuschemeng.1c03891.Peer-Reviewed Original Research