Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides

Raffaele Senatore, Laura Ielo, Ernst Urban, Wolfgang Holzer, Vittorio Pace (Corresponding author)

    Publications: Contribution to journalArticlePeer Reviewed

    Abstract

    The proper generation of α-​thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-​oxo thioethers. The procedure is adaptable to alkyl- or aryl- thiomethyllithium conjugates. It has the advantages of conceptual simplicity and versatility of the addn. of organometallics to Weinreb amides with the possibility to fully preserve the optical information contained in the starting materials.
    Original languageEnglish
    Pages (from-to)2466-2470
    Number of pages5
    JournalEuropean Journal of Organic Chemistry
    Volume2018
    Issue number20-21
    DOIs
    Publication statusPublished - 7 Jun 2018

    Austrian Fields of Science 2012

    • 104015 Organic chemistry

    Keywords

    • Homologation
    • Lithiation
    • Weinreb amides
    • Sulfur
    • Ketones
    • SULFENYLATED CARBONYL-COMPOUNDS
    • CHLOROMETHYL ETHYL ETHER
    • EFFICIENT SYNTHESIS
    • LITHIUM CARBENOIDS
    • KETO THIOETHERS
    • STRAIGHTFORWARD ACCESS
    • ORGANIC-SYNTHESIS
    • HIGHLY EFFICIENT
    • BOND FORMATION
    • ISOCYANATES
    • REAGENTS
    • HALOMETHYLLITHIUMS
    • CATALYST

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