Ytterbium triflate and high pressure-mediated ring opening of epoxides with amines

Masaki Meguro, Naoki Asao, Yoshinori Yamamoto

    Research output: Contribution to journalArticle

    143 Citations (Scopus)

    Abstract

    Ring opening of epoxides with amines in THF takes place very readily in the presence of catalytic amounts of ytterbium triflate to give the corresponding β-amino alcohols in good to high yields. With tri- and tetra-substituted epoxides, the use of an excess (2-3 equiv.) of the amine is needed. The Yb(OTf)3-catalysed reaction of epoxides with amines in CH 2Cl2 is quite complex; the yield of amino alcohols is generally lower and depends upon the addition order of the catalyst, amine and epoxide. The ring opening is accomplished also under high pressures in the absence of Yb(OTf)3. Ring opening with a combination of Yb(OTf) 3 in CH2Cl2 and high pressure is more effective than the use, independently, of either Yb(OTf)3 or the high-pressure method. Oxetanes and β-lactones undergo ring opening in the presence of Yb(OTf)3.

    Original languageEnglish
    Pages (from-to)2597-2601
    Number of pages5
    JournalJournal of the Chemical Society, Perkin Transactions 1
    Issue number18
    DOIs
    Publication statusPublished - 1994

    ASJC Scopus subject areas

    • Chemistry(all)

    Fingerprint Dive into the research topics of 'Ytterbium triflate and high pressure-mediated ring opening of epoxides with amines'. Together they form a unique fingerprint.

  • Cite this