2017
Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids
Key HM, Miller SJ. Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids. Journal Of The American Chemical Society 2017, 139: 15460-15466. PMID: 28975793, PMCID: PMC5736372, DOI: 10.1021/jacs.7b08775.Peer-Reviewed Original ResearchConceptsComplex moleculesSite-selective catalysisComplex molecular settingsComplex natural productsSite-selective modificationPotassium saltNew analoguesApplication of RhFunctional group toleranceEnantioselective catalysisSelective functionalizationCatalyst systemAnalogous reactionStereoselective functionalizationEnantioselective synthesisGroup toleranceNatural productsActive moleculesPotent antibacterial propertiesDehydroalanine residuesBiological testingAmino estersHigh stereoselectivityAntibacterial propertiesMolecular setting
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 interestCatalystEnantioinductionCrystallographyEnantioselectivityIsomersRegioselective Derivatizations of a Tribrominated Atropisomeric Benzamide Scaffold
Barrett KT, Miller SJ. Regioselective Derivatizations of a Tribrominated Atropisomeric Benzamide Scaffold. Organic Letters 2015, 17: 580-583. PMID: 25582814, PMCID: PMC4364386, DOI: 10.1021/ol503593y.Peer-Reviewed Original ResearchConceptsLithium-halogen exchangeAsymmetric ligandsBenzamide scaffoldChiral moleculesRegioselective derivatizationEnantioselective synthesisGroup installationRegioselective transformationSequential PdAllylic alkylationHigh regioselectivityMoleculesBenzamidesPhosphinoDerivatizationRegioselectivityAlkylationLigandsTribromideSynthesisDerivativesPdScaffoldsPotential utility
2013
Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination
Barrett KT, Miller SJ. Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination. Journal Of The American Chemical Society 2013, 135: 2963-2966. PMID: 23410090, PMCID: PMC3596792, DOI: 10.1021/ja400082x.Peer-Reviewed Original ResearchConceptsEnantioselective synthesisElectrophilic aromatic substitution reactionsSeries of triAromatic substitution reactionMetal-halogen exchangeRange of compoundsCatalytic brominationNMR spectroscopySubstitution reactionsBrønsted baseObserved productsOrtho functionalizationTertiary aminesLow conversionSubstitution patternBrominationCatalystHigh barrierBenzamidesReactionTertiary benzamidesAppropriate substrateSynthesisFunctionalizationDibromination