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Synlett 1992; 1992(3): 214-216
DOI: 10.1055/s-1992-21317
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Cycloadditions of Carbonyl Oxides: A Novel Stereoselective Approach to 1,3-Diols

Mike Casey* , Andrew J. Culshaw
  • *Department of Chemistry and Applied Chemistry, University of Salford, Salford M5 4WT, England
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Publication Date:
08 March 2002 (online)

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Carbonyl oxides, formed by ozonolysis of enol ethers [e.g., 1-methoxy-4,8-dimethylnona-1,7-diene (4)], undergo stereoselective intramolecular cycloadditions to unactivated alkenes to give bicyclic dioxolanes. The dioxolanes were easily transformed by catalytic hydrogenation into ß-hydroxycarbonyl compounds and 1,3-diols, thus providing a novel route to 1,3-dioxygenated products.