Facile synthesis of aliphatic isothiocyanates and thioureas on solid phase using peptide coupling reagents

Ulrik Boas, Heidi Gertz Andersen, Jørn B. Christensen, Peter M. H. Heegaard

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    Peptide coupling reagents can be used as versatile reagents for the formation of aliphatic isothiocyanates and thioureas on solid phase from the corresponding solid-phase anchored aliphatic primary amines. The formation of the thioureas is fast and highly chemoselective, and proceeds via formation of the intermediate isothiocyanate. The isothiocyanate and subsequent thiourea formation take place under standard peptide coupling conditions using carbon disulfide as the 'amino acid'. The thioureas are released from the resin and isolated in moderate to high yields.
    Original languageEnglish
    JournalTetrahedron Letters
    Volume45
    Issue number2
    Pages (from-to)269-272
    ISSN0040-4039
    DOIs
    Publication statusPublished - 2004

    Keywords

    • isothiocyanates
    • thioureas solid-phase synthesis
    • peptide coupling reagents
    • combinatorial chemistry

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