Abstract
[reaction: see text] The base-promoted condensation of beta-dicarbonyl compounds with alpha-haloketones, the Feist-Bénary reaction, conveniently produces highly substituted dihydrofurans. We show here that this reaction is quite general with respect to the nature of the beta-dicarbonyl compound, proceeding with beta-ketoesters, beta-oxopropionates, beta-diketones, and beta-dialdehydes. We also show that the diastereoselectivity of this reaction depends on the acidity of the nucleophile.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antifungal Agents / chemistry
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
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Enzyme Inhibitors / chemical synthesis
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Farnesyl-Diphosphate Farnesyltransferase / antagonists & inhibitors
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Furans / chemical synthesis*
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Stereoisomerism
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Tricarboxylic Acids / chemical synthesis
Substances
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Antifungal Agents
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Bridged Bicyclo Compounds, Heterocyclic
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Enzyme Inhibitors
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Furans
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Tricarboxylic Acids
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squalestatin 1
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Farnesyl-Diphosphate Farnesyltransferase