Chiral Copper(II) Complex-Catalyzed Reactions of Partially Protected Carbohydrates
Allen CL, Miller SJ. Chiral Copper(II) Complex-Catalyzed Reactions of Partially Protected Carbohydrates. Organic Letters 2013, 15: 6178-6181. PMID: 24274325, DOI: 10.1021/ol4033072.Peer-Reviewed Original ResearchConceptsCoupling of electrophilesCarbohydrate chemistryDivergent regioselectivityRegioselective functionalizationCatalyzed reactionsSaccharide moleculesSuch reactionsCatalystReactionManipulation stepsFunctionalizationChemistryElectrophilesChiralRegioselectivityEnantiomersSynthesisMoleculesHereinCopperSugarsEnantioselective 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