2022
Catalytic Enantioselective Sulfur Alkylation of Sulfenamides for the Asymmetric Synthesis of Sulfoximines
Greenwood NS, Champlin AT, Ellman JA. Catalytic Enantioselective Sulfur Alkylation of Sulfenamides for the Asymmetric Synthesis of Sulfoximines. Journal Of The American Chemical Society 2022, 144: 17808-17814. PMID: 36154032, PMCID: PMC9650615, DOI: 10.1021/jacs.2c09158.Peer-Reviewed Original ResearchConceptsAsymmetric synthesisAlkylation productsChiral sulfur centerChiral rhodium catalystNew asymmetric synthesisDifferent binding interactionsChiral sulfoximinesChallenging preparationDiazo compoundsRhodium catalystSingle enantiomerNitrogen substituentsSulfur centerMild conditionsSulfur alkylationBinding interactionsRacemic mixtureDrug discoveryEnantiomeric ratioAlkylationHigh yieldsComplete retentionSynthesisKey stepEnantiomers
2004
Asymmetric α-Alkylation of N ‘-tert-Butanesulfinyl Amidines. Application to the Total Synthesis of (6R,7S)-7-Amino-7,8-dihydro-α-bisabolene
Kochi T, Ellman JA. Asymmetric α-Alkylation of N ‘-tert-Butanesulfinyl Amidines. Application to the Total Synthesis of (6R,7S)-7-Amino-7,8-dihydro-α-bisabolene. Journal Of The American Chemical Society 2004, 126: 15652-15653. PMID: 15571381, DOI: 10.1021/ja044753n.Peer-Reviewed Original Research
1999
Chiral N-Acyl-tert-butanesulfinamides: The “Safety-Catch” Principle Applied to Diastereoselective Enolate Alkylations
Backes BJ, Dragoli DR, Ellman JA. Chiral N-Acyl-tert-butanesulfinamides: The “Safety-Catch” Principle Applied to Diastereoselective Enolate Alkylations. The Journal Of Organic Chemistry 1999, 64: 5472-5478. PMID: 11674609, DOI: 10.1021/jo990271w.Peer-Reviewed Original ResearchAlkylation reactionDiastereoselective C-alkylationSolid-phase synthesisDiastereoselective enolate alkylationTarget compoundsN-alkylationChiral alcoholsChiral auxiliariesEnantiopure productsC-alkylationEnolate alkylationSulfinamidesButanesulfinamidesAlkylation productsHigh diastereoselectivityS-oxidationEster equivalentsCompoundsAcylationReactionAuxiliariesConversionSafety catchChiralAlkylation
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