Hydrolysis rates of alkyl and aryl sulfinamides: evidence of general acid catalysis

Andrew M. Piggott, Peter Karuso*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    Sulfinamides are important in enantioselective synthesis, as rare post-translational modifications of proteins and as isosteres of the amide bond. Little is known about the rates of hydrolysis for aliphatic sulfinamides or the mechanism of hydrolysis. In this Letter, we show that sulfinamides hydrolyse by predominantly a non-specific acid/base catalysis with phosphate buffer but by varying the buffer concentration, it was possible to determine the hydrolysis rates of a range of sulfinamides with water through non-linear least squares regression.

    Original languageEnglish
    Pages (from-to)7452-7455
    Number of pages4
    JournalTetrahedron Letters
    Volume48
    Issue number42
    DOIs
    Publication statusPublished - 15 Oct 2007

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