2024
Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides
Huth S, Tampellini N, Guerrero M, Miller S. Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides. Organic Letters 2024, 26: 6872-6877. PMID: 39102356, PMCID: PMC11329351, DOI: 10.1021/acs.orglett.4c02452.Peer-Reviewed Original ResearchConceptsEnantioselective oxidation of sulfidesModel of transition stateLevels of enantioinductionOxidation of sulfidesChiral sulfoxidesPeptide catalystsTransition stateEnantioselective sulfoxidationAspartic acid-containing peptidesSulfoxideThioethersEnantioinductionCatalystMoietySubstrateHydrogenSulfideExperimental evidence
1998
Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines
Cogan D, Liu G, Kim K, Backes B, Ellman J. Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines. Journal Of The American Chemical Society 1998, 120: 8011-8019. DOI: 10.1021/ja9809206.Peer-Reviewed Original ResearchCatalytic asymmetric oxidationTert-butyl disulfideAsymmetric oxidationChiral Schiff base ligandsEster 2Schiff base ligandTert-butyl sulfoxidesBase ligandStoichiometric oxidantChiral sulfoxidesGrignard reagentsTert-butanesulfinamideExcellent precursorDisulfide 1Liquid ammoniaLithium amideNucleophilic displacementGood yieldsEnantiomeric excessOverall yieldFirst exampleSingle recrystallizationOxidationSulfoxideDisulfide
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