σ-π chelation-controlled chemoselective ring openings of epoxides

Naoki Asao, Taisuke Kasahara, Yoshinori Yamamoto

    Research output: Contribution to journalArticle

    13 Citations (Scopus)

    Abstract

    The chemoselective ring opening of alkynyl epoxides in the co-existence of the corresponding alkyl epoxides is achieved in the Me3Al mediated reaction with alkynyllithium reagents. The observed interesting chemoselectivity is most probably a reflection of bidentate complexation of the Lewis acid to an n-electron of an oxygen atom of the epoxide and π-electrons of the C-C triple bond.

    Original languageEnglish
    Pages (from-to)7903-7905
    Number of pages3
    JournalTetrahedron Letters
    Volume42
    Issue number44
    DOIs
    Publication statusPublished - 2001 Oct 29

    Keywords

    • Alkynes
    • Chemoselectivity
    • Coordination modes
    • Epoxides
    • Lewis acids

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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