Palladium-catalyzed [3+2] cycloaddition of carbon dioxide and trimethylenemethane under mild conditions
Palladium-catalyzed [3+2] cycloaddition of carbon dioxide and trimethylenemethane under mild conditions
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DOI：
10.1021/ol7017246
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发表时间：
2007-09-13
期刊：
影响因子：
5.2
通讯作者：
Worthy, Amanda D.
中科院分区：
文献类型：
--
作者：
Greco, George E.;Gleason, Brittany L.;Worthy, Amanda D.
当Pd-TMM络合物由2-（乙酰氧基甲基）-3-（三甲基甲硅烷基）丙烯产生时，二氧化碳与三亚甲基甲烷（TMM）在温和条件（1大气压，75 ℃，30分钟）下经历Pd催化的[3+2]环加成，以63%的产率产生γ-丁内酯产物。这里报道的反应比全碳[3+2]环加成反应更快，并且在竞争实验中仅产生γ-丁内酯。与取代的底物，反应是完全区域选择性的，产生的产品来自动力学Pd-TMM复合物。
Carbon dioxide undergoes a Pd-catalyzed [3+2] cycloaddition with trimethylenemethane (TMM) under mild conditions (1 atm, 75 degrees C, 30 min) to produce a gamma-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 gamma-butyrolactone is produced in a competition experiment. With substituted substrates, the reaction is completely regioselective, producing the product derived from the kinetic Pd-TMM complex.