期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 1, 页码 370-374出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo802103g
关键词
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资金
- Korea Science and Engineering Foundation (KOSEF) [R01-2007-000-20315-0]
- National Research Foundation of Korea [R01-2007-000-20315-0, 2007-0055274, 과06A1507] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
Atom-economical syntheses of isomeric 5-acetoxy-2-alkyl-2-cyclopentenones (2) and acetoxymethyl (x-alkylailen ones (3) have been described via Au-catalyzed hydrative rearrangement of 1,1-diethynyl-carbinol 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.
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