Understanding the reactivity of acyl anion equivalents: the epoxide ring opening case

W. Eger, R. Grange, H. Schill, R. Goumont, Tim Clark, C. Williams

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.
    Original languageEnglish
    Pages (from-to)2548-2553
    Number of pages6
    JournalEuropean Journal of Organic Chemistry
    Volume2011
    Issue number3
    DOIs
    Publication statusPublished - May 2011

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