Probing the Efficiency of N-Heterocyclic Carbene Promoted O- to C-Carboxyl Transfer of Oxazolyl Carbonates
The Journal of Organic Chemistry2008Vol. 73(7), pp. 2784–2791
Citations Over TimeTop 10% of 2008 papers
Jennifer E. Thomson, Craig D. Campbell, Carmen Concellón, Nicolas Duguet, Kathryn Rix, Alexandra M. Z. Slawin, Andrew D. Smith
Abstract
Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at <1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.
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