Au(I)-Catalyzed Hydrative Rearrangement of 1,1-Diethynylcarbinol Acetates to Functionalized Cyclopentenones and Allenones

Chang Ho Oh* and Swastik Karmakar

*Department of Chemistry, Hanyang University, Sungdong-Gu, Seoul 133-791, South Korea, Email: changhohanyang.ac.kr

C. H. Oh, S. Karmakar, J. Org. Chem., 2009, 74, 370-374.

DOI: 10.1021/jo802103g

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Abstract

The Au-catalyzed hydrative rearrangement of 1,1-diethynylcarbinol acetates in wet CH₂Cl₂ produces either 5-acetoxy-2-alkyl-2-cyclopentenones or acetoxymethyl α-alkylallenones as a major product depending on the temperature, reaction time, and catalyst loading.

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Key Words

Cyclopentenones, Rearrangements, Hydration

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ID: J42-Y2009-0060