Feist–Benary synthesis: Difference between revisions

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[[Image:FeistBenarysynthesis.gif|center|Feist Benary synthesis]]
 
A recent modification is the [[enantioselective]] '''interrupted Feist-Benary reaction''' {{Ref|3}} with a [[chiral auxiliary]] based on the [[cinchona]] [[alkaloid]] [[quinine]] based in the presence of [[proton sponge]] to the hydroxydihydrofuran. This type of alkaloids is also used in asymmetric synthesis in the [[AD-mix]]. The alkaloid is [[protonation|protonated]] throughout the reaction and transfers its [[Chirality (chemistry)|chirality]] by interaction of the acidic [[ammonium salt|ammonium]] hydrogen with the dicarbonyl group of [[pyruvate|ethyl bromopyruvate]] in a 5-membered [[transition state]].
 
[[Image:InterruptedFeistBenary.gif|center|interrupted Feist-Benary reaction]]