Stereoselective α,α'-annelation reactions of 1,3-dioxan-5-ones

Tyrone Casey, J Carlisle, P Tisselli, Louise Male, Neil Spencer, Richard Grainger

Research output: Contribution to journalArticle

11 Citations (Scopus)


Pyrrolidine enamines derived from three 1,3-dioxan-5-ones undergo (alpha,alpha'-annelation reactions with methyl alpha-(bromomethyl)acrylate to produce bridged 2,4-dioxabicyclo[3.3.1]-nonane ring systems with complete stereocontrol. Stereochemical outcomes have been rationalized based on steric and stereoelectronic interactions in intermediate boat-like conformations of the 1,3-dioxane ring and subsequent kinetic protonation to set an axial ester group on the cyclohexanone ring. Base-mediated ester epimerization provides the stereochemical array found in the highly oxygenated cyclohexane ring of phyllaemblic acid and glochicoccins B and D.
Original languageEnglish
Pages (from-to)7461-7464
Number of pages4
JournalThe Journal of Organic Chemistry
Issue number21
Early online date11 Oct 2010
Publication statusPublished - 5 Nov 2010


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