2024
Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie 2024, 136 DOI: 10.1002/ange.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalystEnantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie International Edition 2024, 63: e202408820. PMID: 39058627, PMCID: PMC11514311, DOI: 10.1002/anie.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalystRh(II)-Catalyzed Enantioselective S‑Alkylation of Sulfenamides with Acceptor–Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality
Patel S, Greenwood N, Mercado B, Ellman J. Rh(II)-Catalyzed Enantioselective S‑Alkylation of Sulfenamides with Acceptor–Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality. Organic Letters 2024, 26: 6295-6300. PMID: 39004842, PMCID: PMC11292377, DOI: 10.1021/acs.orglett.4c02402.Peer-Reviewed Original Research
2023
Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie International Edition 2023, 63: e202315701. PMID: 38015869, PMCID: PMC10813656, DOI: 10.1002/anie.202315701.Peer-Reviewed Original ResearchS bond formationOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidSynthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie 2023, 136 DOI: 10.1002/ange.202315701.Peer-Reviewed Original ResearchOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidStyrene