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• W2150869518 endingPage "14680" @default.
• W2150869518 startingPage "14675" @default.
• W2150869518 abstract "The conjugate addition of carbonyl anions catalyzed by thiazolium salts that is fully operative under neutral aqueous conditions has been accomplished. The combination of α-keto carboxylates and thiazolium-derived zwitterions produces reactive carbonyl anions in a buffered protic environment that readily undergo conjugate additions to substituted α,β-unsaturated 2-acyl imidazoles. The scope of the reaction has been examined and found to accommodate various α-keto carboxylates and β-aryl substituted unsaturated 2-acyl imidazoles. The optimal precatalyst for this process is the commercially available thiazolium salt 5, a simple analogue of thiamin diphosphate. In this process, no benzoin products from carbonyl anion dimerization are observed. The corresponding 1,4-dicarbonyl compounds can be efficiently converted into esters and amides by way of activation of the N-methylimidazole ring via alkylation." @default.
• W2150869518 created "2016-06-24" @default.
• W2150869518 creator A5041041100 @default.
• W2150869518 creator A5042593880 @default.
• W2150869518 creator A5070561855 @default.
• W2150869518 creator A5072698857 @default.
• W2150869518 date "2005-10-01" @default.
• W2150869518 modified "2023-09-30" @default.
• W2150869518 title "Catalytic Conjugate Additions of Carbonyl Anions under Neutral Aqueous Conditions" @default.
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• W2150869518 doi "https://doi.org/10.1021/ja0520161" @default.
• W2150869518 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16231921" @default.
• W2150869518 hasPublicationYear "2005" @default.
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