2025
Enantioselective Hydrodifluoroalkylation of Alkenes with Conformationally Tuned Peptidyl Hydrogen Atom Transfer Catalysts
Pereira M, Geunes E, Shao H, Zhang Y, Cheng J, Magpantay S, Mercado B, Mayer J, Houk K, Knowles R, Miller S. Enantioselective Hydrodifluoroalkylation of Alkenes with Conformationally Tuned Peptidyl Hydrogen Atom Transfer Catalysts. Journal Of The American Chemical Society 2025, 147: 11412-11424. PMID: 40111502, PMCID: PMC11983094, DOI: 10.1021/jacs.5c01166.Peer-Reviewed Original ResearchConceptsHydrogen atom transferHydrogen atom transfer catalystCarbon-carbon bond formationX-ray crystallographic analysisCarbon-centered radicalsChiral catalystsAsymmetric inductionAtom transferDFT calculationsPhotocatalytic generationTransfer catalystCrystallographic analysisBond formationEnantiomeric ratioCatalystX-rayAlkenesRadicalsDFTTrialkylaminesAmideConformationCysteineTetrapeptideResiduesEnantiocontrolled Cyclization to Form Chiral 7- and 8‑Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms
Tampellini N, Mercado B, Miller S. Enantiocontrolled Cyclization to Form Chiral 7- and 8‑Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms. Journal Of The American Chemical Society 2025, 147: 4624-4630. PMID: 39847512, PMCID: PMC11815475, DOI: 10.1021/jacs.4c17080.Peer-Reviewed Original ResearchApplication of asymmetric catalysisCyclization of substratesMedium-sized ringsSeven-membered ringEight-membered ringAxis of chiralitySingle bond axisChiral catalystsOrganocatalytic strategyAsymmetric catalysisCyclization methodStereogenic atomsCyclization reactionCyclization stepRing sizeMild conditionsCyclizationCatalystRingChiralityReactionMechanistic paradigmEnantiocontrolStereocontrolSterically
2019
α-Branched amines by catalytic 1,1-addition of C–H bonds and aminating agents to terminal alkenes
Maity S, Potter TJ, Ellman JA. α-Branched amines by catalytic 1,1-addition of C–H bonds and aminating agents to terminal alkenes. Nature Catalysis 2019, 2: 756-762. PMID: 32879907, PMCID: PMC7462361, DOI: 10.1038/s41929-019-0330-7.Peer-Reviewed Original ResearchTerminal alkenesH bond substratesOne-step synthesisHigh functional group compatibilityFunctional group compatibilityChiral catalystsBranched aminesFeedstock chemicalsConvergent synthesisH bondsAsymmetric synthesisN bondAddition pathwayRhodium precatalystGroup compatibilityMild conditionsBond substratesIntermolecular formationDrug structureAminesSynthesisAlkenesClinical candidatesBondsΑ-methyl
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