Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles

Nathalie Batoux, Christopher Hardacre, Marie E. Migaud, Kerry A. Ness, Sarah E. Norman

    Research output: Contribution to journalArticlepeer-review

    Abstract

    1,2-Cyclic sulfite xylosides offer facile access to 1,2-oxazolines upon reaction with aromatic and alkyl nitriles under Lewis or Brönsted acid conditions. Additionally, hydrophobic ionic liquids facilitate acid-catalysed formations of such oxazolines and C- and O-linked xylosides, providing means to carry out fast reactions at room temperature, and this in yields comparable to reactions conducted in xylene at high temperature for extended reaction time.

    Original languageEnglish
    Pages (from-to)8858-8862
    Number of pages5
    JournalTetrahedron
    Volume65
    Issue number43
    DOIs
    Publication statusPublished - 24 Oct 2009

    Keywords

    • C-, O-linked furanosides
    • C-nucleosides
    • Cyclic sulfites
    • Ionic liquids
    • Oxazoline

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