N-heterocyclic carbene cascade catalysis: Dual Bronsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones

Lisa Candish, David Lupton

Research output: Contribution to journalArticleResearchpeer-review

60 Citations (Scopus)

Abstract

The first example of Bronsted/Lewis base cascade catalysis using an N-heterocyclic carbene has been realised through the rearrangement of cyclopropyl esters to dihydropyranones. The scope and mechanism of this transformation has been examined implicating a novel NHC-mediated electrocyclic cyclopropane rearrangement followed by an anionic oxy Claisen-rearrangement.
Original languageEnglish
Pages (from-to)380 - 383
Number of pages4
JournalChemical Science
Volume3
Issue number2
DOIs
Publication statusPublished - 2012

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