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• W2085432810 endingPage "374" @default.
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• W2085432810 abstract "Atom-economical syntheses of isomeric 5-acetoxy-2-alkyl-2-cyclopentenones (2) and acetoxymethyl α-alkylallenones (3) have been described via Au-catalyzed hydrative rearrangement of 1,1-diethynylcarbinol acetates (1). In anhydrous condition, Au(I)-catalyzed [3,3]-rearrangement of 1 afforded the 3-alkynylallenyl acetate 4 in low yield. Treatment of 1 with Au(I) catalyst in wet CH2Cl2 produced either 2 or 3 as a major product depending on the temperature, reaction time, and catalyst loading. D has been proposed as an intermediate, which might be formed via Au(I)-induced internal oxacyclization of the intermediate 4 followed by chemoselective nucleophilic attack by the water molecule. Formation of 2 or 3 might be explained via sequential 1,3-dioxole ring opening and gold-promoted 5-endo-dig carbocyclization or simple protonation of the intermediate D, respectively." @default.
• W2085432810 created "2016-06-24" @default.
• W2085432810 creator A5026899068 @default.
• W2085432810 creator A5071460667 @default.
• W2085432810 date "2008-11-21" @default.
• W2085432810 modified "2023-10-01" @default.
• W2085432810 title "Au(I)-Catalyzed Hydrative Rearrangement of 1,1-Diethynylcarbinol Acetates to Functionalized Cyclopentenones and Allenones" @default.
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• W2085432810 doi "https://doi.org/10.1021/jo802103g" @default.
• W2085432810 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19053596" @default.
• W2085432810 hasPublicationYear "2008" @default.
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