2024
Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie 2024, 136 DOI: 10.1002/ange.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalystEnantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie International Edition 2024, 63: e202408820. PMID: 39058627, PMCID: PMC11514311, DOI: 10.1002/anie.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalyst
2023
Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie International Edition 2023, 63: e202315701. PMID: 38015869, PMCID: PMC10813656, DOI: 10.1002/anie.202315701.Peer-Reviewed Original ResearchS bond formationOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidSynthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie 2023, 136 DOI: 10.1002/ange.202315701.Peer-Reviewed Original ResearchOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidStyrene
2017
Base‐Controlled Completely Selective Linear or Branched Rhodium(I)‐Catalyzed C−H ortho‐Alkylation of Azines without Preactivation
Tran G, Hesp K, Mascitti V, Ellman J. Base‐Controlled Completely Selective Linear or Branched Rhodium(I)‐Catalyzed C−H ortho‐Alkylation of Azines without Preactivation. Angewandte Chemie 2017, 129: 5993-5997. DOI: 10.1002/ange.201702409.Peer-Reviewed Original ResearchCatalytic systemBranched selectivityExcellent functional group compatibilityComplete branched selectivityFunctional group compatibilityQuaternary carbon centerBranched alkylationOrtho alkylationEthyl methacrylateOperational simplicityCarbon centerGroup compatibilitySelective linearAzinesCatalytic baseRapid accessSelectivityAlkylationComplete linearBroad scopeAcrylateMethacrylateAcrylamidePharmaceuticalsLinearBase‐Controlled Completely Selective Linear or Branched Rhodium(I)‐Catalyzed C−H ortho‐Alkylation of Azines without Preactivation
Tran G, Hesp KD, Mascitti V, Ellman JA. Base‐Controlled Completely Selective Linear or Branched Rhodium(I)‐Catalyzed C−H ortho‐Alkylation of Azines without Preactivation. Angewandte Chemie International Edition 2017, 56: 5899-5903. PMID: 28429455, PMCID: PMC5558092, DOI: 10.1002/anie.201702409.Peer-Reviewed Original ResearchConceptsCatalytic systemBranched selectivityExcellent functional group compatibilityComplete branched selectivityFunctional group compatibilityQuaternary carbon centerBranched alkylationOrtho alkylationEthyl methacrylateOperational simplicityH alkylationCarbon centerGroup compatibilitySelective linearAzinesCatalytic baseRapid accessSelectivityAlkylationComplete linearBroad scopeAcrylateMethacrylateAcrylamidePharmaceuticals
2016
Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C–H Conjugate Addition/Cyclization Reactions
Weinstein AB, Ellman JA. Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C–H Conjugate Addition/Cyclization Reactions. Organic Letters 2016, 18: 3294-3297. PMID: 27337641, PMCID: PMC4973575, DOI: 10.1021/acs.orglett.6b01611.Peer-Reviewed Original ResearchConceptsAddition/cyclization reactionNitrogen heterocyclesCyclization reactionAlkaloid natural productsDiverse nitrogen heterocyclesTricyclic nitrogen heterocyclesConvergent synthesisEfficient synthesisElectrophilic olefinsHeteroaromatic productsNatural productsCyclic imidesDirecting groupHeterocyclesSynthesisBroad scopeReactionOlefinsImideOxoassoanineAmidesProductsSubstrate
2012
Rhodium( iii )-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes
Lian Y, Bergman RG, Ellman JA. Rhodium( iii )-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes. Chemical Science 2012, 3: 3088-3092. PMID: 23050074, PMCID: PMC3462028, DOI: 10.1039/c2sc20835k.Peer-Reviewed Original Research
2008
Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation
Colby DA, Bergman RG, Ellman JA. Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation. Journal Of The American Chemical Society 2008, 130: 3645-3651. PMID: 18302381, PMCID: PMC3057408, DOI: 10.1021/ja7104784.Peer-Reviewed Original ResearchConceptsSynthesis of dihydropyridinesReductive elimination stepOne-pot CX-ray analysisFacile COxidative additionDihydropyridine intermediatesPyridine derivativesH activationStructure determinationElimination stepAromatization sequenceRate constantsAlkynesLigandsNew classSynthesisKinetic simulationsBroad scopePyridineIminesKetiminesAldiminesIntermediatesComplexes
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