2015
Regioselective 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