A synthetic alternative to the Type-II intramolecular 4+3 cycloaddition reaction

Richard Grainger, RB Owoare, P Tisselli, JW Steed

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.
Original languageEnglish
Pages (from-to)7899-7902
Number of pages4
JournalThe Journal of Organic Chemistry
Volume68
Issue number20
Early online date9 Sep 2003
DOIs
Publication statusPublished - 1 Oct 2003

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