N-heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with alpha,beta-unsaturated acid fluorides

Sarah Ryan, Lisa Candish, David Lupton

Research output: Contribution to journalArticleResearchpeer-review

181 Citations (Scopus)

Abstract

Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with alpha,beta-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr > 20:1) while demonstrating a new type of reaction cascade exploiting alpha,beta-unsaturated acyl azoliums.
Original languageEnglish
Pages (from-to)4694 - 4697
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number13
DOIs
Publication statusPublished - 2011

Cite this