Scope and diastereoselectivity of the "interrupted" Feist-Bénary reaction.
[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.
Calter
Michael A
MA
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. calter@chem.rochester.edu
Zhu
Cheng
C
D000935:Antifungal Agents / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D013186:Farnesyl-Diphosphate Farnesyltransferase / Q000037:antagonists & inhibitors; D005663:Furans / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014233:Tricarboxylic Acids / Q000138:chemical synthesis
D000935:Antifungal Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004791:Enzyme Inhibitors; D005663:Furans; D014233:Tricarboxylic Acids; C075117:squalestatin 1; D013186:Farnesyl-Diphosphate Farnesyltransferase