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
2011
Iridium-Catalyzed Hydrogenation of N-Heterocyclic Compounds under Mild Conditions by an Outer-Sphere Pathway
Dobereiner GE, Nova A, Schley ND, Hazari N, Miller SJ, Eisenstein O, Crabtree RH. Iridium-Catalyzed Hydrogenation of N-Heterocyclic Compounds under Mild Conditions by an Outer-Sphere Pathway. Journal Of The American Chemical Society 2011, 133: 7547-7562. PMID: 21510610, DOI: 10.1021/ja2014983.Peer-Reviewed Original ResearchMild conditionsHomogeneous iridium catalystN-heterocyclic compoundsOuter-sphere mechanismOuter-sphere pathwayInner-sphere mechanismHydrogenation of quinolineUnprecedentedly mild conditionsIridium hydrideIridium-catalyzed hydrogenationCoordination geometryLigand setUnhindered substratesCatalyst precursorsSequential protonCatalytic experimentsCatalytic reactionIridium catalystDFT calculationsDihydride complexCatalyst activityDFT studyHydride transferMechanistic proposalComplex show