2024
Carbocation Mechanism Revelation of Molecular Iodine-Mediated Dehydrogenative Aromatization of Substituted Cyclic Ketones to Phenols
Jin Y, Petrovic P, Huang S, Banerjee S, Nandy A, Anastas P, Lam J. Carbocation Mechanism Revelation of Molecular Iodine-Mediated Dehydrogenative Aromatization of Substituted Cyclic Ketones to Phenols. The Journal Of Organic Chemistry 2024, 89: 3226-3237. PMID: 38361498, DOI: 10.1021/acs.joc.3c02691.Peer-Reviewed Original ResearchDehydrogenative aromatizationCyclic ketonesDesorption electrospray ionization-mass spectrometryC-H bond activationElectrospray ionization-mass spectrometrySubstrate scope studyUnsaturated cyclic ketonesIonization-mass spectrometryHigh energy barrierProton nuclear magnetic resonanceMass spectrometric analysisBond activationSubstrate scopeDFT calculationsNuclear magnetic resonanceProduct selectivityPhenol etherReaction mechanismCarbocationProduct distributionSpectrometric analysisKetonesWater boiling temperatureAmbient conditionsAromatic precursors
2015
Enantioselective Synthesis of 3‑Arylquinazolin-4(3H)‑ones via Peptide-Catalyzed Atroposelective Bromination
Diener ME, Metrano AJ, Kusano S, Miller SJ. Enantioselective Synthesis of 3‑Arylquinazolin-4(3H)‑ones via Peptide-Catalyzed Atroposelective Bromination. Journal Of The American Chemical Society 2015, 137: 12369-12377. PMID: 26343278, PMCID: PMC5134330, DOI: 10.1021/jacs.5b07726.Peer-Reviewed Original ResearchConceptsAtroposelective brominationDensity functional theory calculationsBroad substrate scopeX-ray crystallographyΒ-turn peptideFunctional theory calculationsCross-coupling sequenceFree catalystsSubstrate scopeAmination procedureStereochemical informationEnantioselective synthesisTheory calculationsHigh enantioselectivityRotational barriersMechanistic studiesSubsequent transformationBrominationMono-orthoProduct of interestCatalystEnantioinductionCrystallographyEnantioselectivityIsomers
2014
Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation.
Abascal NC, Lichtor PA, Giuliano MW, Miller SJ. Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation. Chemical Science 2014, 5: 4504-4511. PMID: 25386335, PMCID: PMC4224318, DOI: 10.1039/c4sc01440e.Peer-Reviewed Original ResearchA Lewis Acid Catalyzed Annulation to 2,1-Benzisoxazoles
Otley KD, Ellman JA. A Lewis Acid Catalyzed Annulation to 2,1-Benzisoxazoles. The Journal Of Organic Chemistry 2014, 79: 8296-8303. PMID: 25157596, PMCID: PMC4156248, DOI: 10.1021/jo5015432.Peer-Reviewed Original ResearchConceptsInitial mechanistic investigationsLewis Acid‐Catalyzed AnnulationFriedel-Crafts cyclizationConvergent routeSubstrate scopeReaction intermediatesCompound classesGlyoxylate estersCatalyzed AnnulationO-selectivityUmpolung additionMechanistic investigationsConvenient conditionsHigh yieldsAnnulationBenzisoxazoleDeveloped methodNitrosoarenesNitrosobenzeneCyclizationNew typeIntermediatesSynthesisReactionEstersCo( ii ), a catalyst for selective conversion of phenyl rings to carboxylic acid groups
Sinha S, Campos J, Brudvig G, Crabtree R. Co( ii ), a catalyst for selective conversion of phenyl rings to carboxylic acid groups. RSC Advances 2014, 4: 49395-49399. DOI: 10.1039/c4ra10510a.Peer-Reviewed Original Research
2006
Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates
Schneekloth J, Pucheault M, Crews C. Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates. European Journal Of Organic Chemistry 2006, 2007: 40-43. DOI: 10.1002/ejoc.200600721.Peer-Reviewed Original ResearchNatural product chemistryStraightforward reaction conditionsOrganic chemistryProduct chemistryOrganozinc reagentsSubstrate scopeReaction conditionsPalladium precatalystsHigh selectivityZ selectivityCross couplingSelectivityChemistryReactionLigandsDieneInteresting reversalPrecatalystOlefinsReagentsProductsAcetateAssemblyBroad useAppropriate choice
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