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

Research output: Contribution to journalArticlepeer-review

  • W. Eger
  • R. Grange
  • H. Schill
  • R. Goumont
  • Tim Clark
  • C. Williams
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
Issue number3
Publication statusPublished - May 2011

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