Palladium-Catalyzed [3+2] Cycloaddition of Carbon Dioxide and Trimethylenemethane under Mild Conditions

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• 作者：George E. Greco ; Brittany L. Gleason ; Tiffany A. Lowery ; Matthew J. Kier ; Lisa B. Hollander ; Shoshanah A. Gibbs ; Amanda D. Worthy
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：September 13, 2007
• 年：2007
• 卷：9
• 期：19
• 页码：3817 - 3820
• 全文大小：68K
• 年卷期：v.9,no.19(September 13, 2007)
• ISSN：1523-7052

文摘

Carbon dioxide undergoes a Pd-catalyzed [3+2] cycloaddition with trimethylenemethane (TMM) under mild conditions (1 atm, 75 C, 30 min)to produce a -butyrolactone product in 63% yield, when the Pd-TMM complex is generated from 2-(acetoxymethyl)-3-(trimethylsilyl)propene.The reaction reported here is more rapid than the all-carbon [3+2] cycloaddition, and only the -butyrolactone is produced in a competitionexperiment. With substituted substrates, the reaction is completely regioselective, producing the product derived from the kinetic Pd-TMMcomplex.