title: Aminooxylation Horner-Wadsworth-Emmons Sequence for the Synthesis of Enantioenriched γ-Functionalized Vinyl Sulfones.
abstract: An operationally simple protocol for the synthesis of γ-hydroxy vinyl sulfones has been developed using a proline-based aldehyde aminooxylation, followed by a vinyl sulfone forming Horner-Wadsworth-Emmons olefination. The adducts, formed in high enantiopurity, were subsequently converted to γ-azido vinyl sulfones, and azide-alkyne click chemistry enabled the synthesis of vinyl sulfone-based triazoles as potential nonpeptidic cysteine protease inhibitors.
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin , Dublin 4, Ireland.
authors.forename: William
authors.initials: W
authors.lastname: Doherty
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin , Dublin 4, Ireland.
authors.forename: Paul
authors.initials: P
authors.lastname: Evans
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D015853:Cysteine Proteinase Inhibitors; D013450:Sulfones; D014230:Triazoles; C009873:divinyl sulfone