2016
Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis
Featherston AL, Miller SJ. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis. Bioorganic & Medicinal Chemistry 2016, 24: 4871-4874. PMID: 27452284, PMCID: PMC5053897, DOI: 10.1016/j.bmc.2016.07.012.Peer-Reviewed Original Research
2014
Multivalency as a Key Factor for High Activity of Selective Supported Organocatalysts for the Baylis–Hillman Reaction
Goren K, Karabline‐Kuks J, Shiloni Y, Barak‐Kulbak E, Miller SJ, Portnoy M. Multivalency as a Key Factor for High Activity of Selective Supported Organocatalysts for the Baylis–Hillman Reaction. Chemistry - A European Journal 2014, 21: 1191-1197. PMID: 25376519, DOI: 10.1002/chem.201404560.Peer-Reviewed Original ResearchConceptsNew carbon-carbon bondsCarbon-carbon bondsRate-determining proton transferThird generation analoguesMethyl vinyl ketoneBaylis–Hillman reactionAnalogous catalystsDendritic catalystsSupported OrganocatalystsImidazole unitsDendritic effectReaction solventIntermediate adductModel reactionProton transferImidazole moietyActive substratesVinyl ketoneCatalystP-nitrobenzaldehydeReaction yieldMultivalent architectureHigh activityContent of waterHigher generationsCatalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
Romney DK, Colvin SM, Miller SJ. Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones. Journal Of The American Chemical Society 2014, 136: 14019-14022. PMID: 25250713, PMCID: PMC4195385, DOI: 10.1021/ja508757g.Peer-Reviewed Original ResearchMeSH KeywordsCatalysisKetonesKineticsOxidation-ReductionPeptidesStereoisomerismSubstrate SpecificityConceptsBaeyer-Villiger oxidationPeptide-based catalystsHydrogen bonding interactionsTypes of selectivityParallel kinetic resolutionCatalyst controlFunctionalized KetonesCyclic ketonesFunctional groupsNatural productsComplex moleculesKinetic resolutionAsymmetric processEnantioselectivityRegioKetonesOxidationBroad utilityCatalystCatalysisSelectivityAmidesSynthesisMoleculesProducts