Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles

Laura Castoldi, Wolfgang Holzer, Thierry Langer (Corresponding author), Vittorio Pace

    Publications: Contribution to journalArticlePeer Reviewed

    Abstract

    The tetrahedral intermediates generated upon the addition of halolithium carbenoids (LiCH2X and LiCHXY) to Weinreb amides have been intercepted and fully characterized as O-TMS heminals. The commercially available N-trimethylsilyl imidazole is the ideal trapping agent whose employment, combined with a straightforward neutral Alox chromatographic purification, enables the isolation of such labile species. The procedure could be advantageously extended also for obtaining O-TMS heminals from N-acylpyrroles. These intermediates manifest interesting reactivity including as precursors of more complex carbenoids.

    Original languageEnglish
    Pages (from-to)9498-9501
    Number of pages4
    JournalChemical Communications
    Volume53
    Issue number68
    DOIs
    Publication statusPublished - 2017

    Austrian Fields of Science 2012

    • 104001 General chemistry

    Keywords

    • ALKYLATION
    • CHEMOSELECTIVE KETONE SYNTHESIS
    • DIRECT TRANSFORMATION
    • EFFICIENT SYNTHESIS
    • ORGANOLITHIUM REAGENTS
    • ORGANOMETALLIC REAGENTS
    • REACTIVITY CONTROL
    • REDUCTIVE NUCLEOPHILIC-ADDITION
    • SECONDARY AMIDES
    • TRIFLIC ANHYDRIDE

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