2018
Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3‑Arylquinazolin-4(3H)‑ones
Crawford JM, Stone EA, Metrano AJ, Miller SJ, Sigman MS. Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3‑Arylquinazolin-4(3H)‑ones. Journal Of The American Chemical Society 2018, 140: 868-871. PMID: 29300461, PMCID: PMC5817992, DOI: 10.1021/jacs.7b11303.Peer-Reviewed Original Research
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
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