2024
Catalyst–Substrate Pairings for Carbocyclic and Heterocyclic Systems in Atroposelective Quinazolinone Synthesis
Guo M, Miller S. Catalyst–Substrate Pairings for Carbocyclic and Heterocyclic Systems in Atroposelective Quinazolinone Synthesis. ACS Catalysis 2024, 17226-17232. DOI: 10.1021/acscatal.4c05014.Peer-Reviewed Original ResearchChiral phosphoric acidPositive nonlinear effectNon-covalent interactionsQuinazolinone synthesisHeterocyclic systemsCatalyst scaffoldHigh enantioselectivityNitrogen heteroatomsEnantiomeric ratioCatalystReaction developmentCatalytic scaffoldMechanistic studiesEnantioselectivityPhosphoric acidSubstrateCarbocyclesCyclocondensationHeterocyclesHeteroatomsScaffoldsReactionSynthesisReactivityYield
2018
Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones
Shugrue C, Featherston AL, Lackner RM, Lin A, Miller SJ. Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3‑Amidocyclohexanones. The Journal Of Organic Chemistry 2018, 83: 4491-4504. PMID: 29547285, PMCID: PMC5963540, DOI: 10.1021/acs.joc.8b00207.Peer-Reviewed Original ResearchConceptsReductive aminationNumerous reactive sitesPeptide catalystsParallel kinetic resolutionDFT calculationsNMR studiesReactive sitesDivergent selectivitySecondary interactionsNatural productsKinetic resolutionCatalystAminationDivergent stereoselectivitiesCatalyzed Reductive AminationPeptide sequencesSelectivityComplex substratesSubstrateDiastereoselectivityStereoselectivityProductsReactivityPhosphopeptidesPhosphothreonine
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
2015
Site-Selective Reactions with Peptide-Based Catalysts
Giuliano MW, Miller SJ. Site-Selective Reactions with Peptide-Based Catalysts. 2015, 372: 157-201. PMID: 26307403, DOI: 10.1007/128_2015_653.Peer-Reviewed Original Research
2014
Diastereo- and Enantioselective Addition of Anilide-Functionalized Allenoates to N‑Acylimines Catalyzed by a Pyridylalanine-Based Peptide
Mbofana CT, Miller SJ. Diastereo- and Enantioselective Addition of Anilide-Functionalized Allenoates to N‑Acylimines Catalyzed by a Pyridylalanine-Based Peptide. Journal Of The American Chemical Society 2014, 136: 3285-3292. PMID: 24527787, DOI: 10.1021/ja412996f.Peer-Reviewed Original Research
2013
Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors
Gould ND, Allen C, Nam BC, Schepartz A, Miller SJ. Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors. Carbohydrate Research 2013, 382: 36-42. PMID: 24177201, DOI: 10.1016/j.carres.2013.09.011.Peer-Reviewed Original ResearchConceptsLewis acidGlycosylation reactionsCombined Lewis acidControl reactionsSubsequent kinetic studiesCatalytic systemBiomimetic conditionsCarboxylic acidsGlycosyl donorsIrreversible reactionKinetic studiesReactionAcid actsCatalytic componentAcidActive enzymeCarbohydrate-active enzymesCatalystProof of principleReactivityDonorsGlycosylStructure