2024
Rh(II)-Catalyzed Enantioselective S‑Alkylation of Sulfenamides with Acceptor–Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality
Patel S, Greenwood N, Mercado B, Ellman J. Rh(II)-Catalyzed Enantioselective S‑Alkylation of Sulfenamides with Acceptor–Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality. Organic Letters 2024, 26: 6295-6300. PMID: 39004842, PMCID: PMC11292377, DOI: 10.1021/acs.orglett.4c02402.Peer-Reviewed Original Research
2021
Rhodium-Catalyzed C–H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles
Dongbang S, Confair DN, Ellman JA. Rhodium-Catalyzed C–H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles. Accounts Of Chemical Research 2021, 54: 1766-1778. PMID: 33740369, PMCID: PMC8026680, DOI: 10.1021/acs.accounts.1c00027.Peer-Reviewed Original ResearchConceptsNitrogen heterocyclesSilyl groupStereogenic centersVersatile intermediatesElectrocyclization cascadeSynthetic method developmentExcellent functional group compatibilityNatural product synthesisDensity functional theory calculationsComplex polycyclic productsDiverse nitrogen heterocyclesMultiple stereogenic centersMechanistic experimentsFunctional theory calculationsShort reaction sequenceFunctional group compatibilityAddition of hydrideEfficient asymmetric synthesisDrug discovery applicationsContiguous stereogenic centersRegioselective ring openingSynthetic strategyMedicinal chemistryDihydropyridine productsChemical biology
2019
Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII‐Catalyzed Three‐Component C−H Bond Addition to Internally Substituted Dienes and Carbonyls
Dongbang S, Shen Z, Ellman J. Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII‐Catalyzed Three‐Component C−H Bond Addition to Internally Substituted Dienes and Carbonyls. Angewandte Chemie 2019, 131: 12720-12724. DOI: 10.1002/ange.201906633.Peer-Reviewed Original ResearchAcyclic Quaternary CentersRelative stereochemistryHomoallylic alcoholsQuaternary centerThree-component strategyBond activationΣ-bondBond additionStereogenic centersCo IIIHigh diastereoselectivityDieneSequential additionThree-componentStereochemistrySubstrate combinationsAlcoholCarbonylAldehydesBondsKetonesDiastereoselectivitySynthesisReactionSynthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII‐Catalyzed Three‐Component C−H Bond Addition to Internally Substituted Dienes and Carbonyls
Dongbang S, Shen Z, Ellman J. Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII‐Catalyzed Three‐Component C−H Bond Addition to Internally Substituted Dienes and Carbonyls. Angewandte Chemie International Edition 2019, 58: 12590-12594. PMID: 31310435, PMCID: PMC6713593, DOI: 10.1002/anie.201906633.Peer-Reviewed Original ResearchConceptsAcyclic Quaternary CentersRelative stereochemistryHomoallylic alcoholsQuaternary centerH bond activationThree-component strategyBond activationBond additionΣ-bondEfficient COStereogenic centersHigh diastereoselectivitySequential additionDieneThree-componentStereochemistrySubstrate combinationsAlcoholAldehydesCarbonylBondsKetonesDiastereoselectivitySynthesisCOAsymmetric synthesis of (−)-naltrexone
Dongbang S, Pedersen B, Ellman JA. Asymmetric synthesis of (−)-naltrexone. Chemical Science 2019, 10: 535-541. PMID: 30713650, PMCID: PMC6326069, DOI: 10.1039/c8sc03748e.Peer-Reviewed Original ResearchAsymmetric synthesisNatural productsStereogenic centersLongest linear sequenceFirst asymmetric synthesisSharpless asymmetric dihydroxylationTwo-step sequenceAllylic oxidationOxo functionalityAchiral precursorsElectrocyclization cascadeBicyclic frameworkHydroxyl groupsHydride shiftAsymmetric dihydroxylationSharpless dihydroxylationH alkenylationAcidic conditionsEnantioselective Sharpless dihydroxylationBiological activitySynthesisGrewe cyclizationDihydroxylationDisparate biological activitiesLinear sequence
2018
Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C−N Bond‐Forming Cross‐Coupling and Catalyst‐Controlled Atroposelective Cyclodehydration
Kwon Y, Chinn AJ, Kim B, Miller SJ. Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C−N Bond‐Forming Cross‐Coupling and Catalyst‐Controlled Atroposelective Cyclodehydration. Angewandte Chemie International Edition 2018, 57: 6251-6255. PMID: 29637680, PMCID: PMC5964046, DOI: 10.1002/anie.201802963.Peer-Reviewed Original ResearchConceptsAxis of chiralityCopper complexesChiral phosphoric acid catalystChiral copper complexesPhosphoric acid catalystStereogenic carbon centersMultiple stereoisomersCatalytic approachCatalytic reactionStereogenic elementsAcid catalystRemote desymmetrizationCatalyst controlAxial chiralityCarbon centerStereogenic centersCross couplingHigh diastereoselectivityPhosphoric acidCatalystChiralityStereoisomersCyclodehydrationStereogenicityReaction
2017
Convergent Synthesis of α‐Branched Amines by Transition‐Metal‐Catalyzed C−H Bond Additions to Imines
Hummel JR, Ellman JA. Convergent Synthesis of α‐Branched Amines by Transition‐Metal‐Catalyzed C−H Bond Additions to Imines. Israel Journal Of Chemistry 2017, 57: 916-931. PMID: 29332949, PMCID: PMC5760185, DOI: 10.1002/ijch.201700021.Peer-Reviewed Original ResearchH bond additionBond additionH functionalization methodsHigh functional group compatibilityMultiple stereogenic centersFunctional group compatibilityAtom-economic approachEnantioselective catalysisSynthetic methodBranched aminesFunctionalization methodConvergent synthesisAmine productsTransition metalsGroup compatibilityNatural productsStereogenic centersChiral iminesCyclization pathwayIminesAminesWaste byproductEfficient entrySynthesisCatalysis
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