Dearomatizing disrotatory electrocyclic ring closure of lithiated N-benzoyloxazolidines

Jonathan Clayden, Savroop Purewal, Madeleine Helliwell, Simon J. Mantell

    Research output: Contribution to journalArticlepeer-review


    Loss of aromaticity ensues when N-benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis-tricyclic products epimerize to their more stable trans diastereoisomers in aqueous acid.
    Original languageEnglish
    Pages (from-to)1049-1051
    Number of pages2
    JournalAngewandte Chemie - International Edition
    Issue number6
    Publication statusPublished - 15 Mar 2002


    • Amides
    • Cyclization
    • Lithiation
    • Pericyclic reaction
    • Stereoselectivity


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