钯催化下乙烯基双环[1.1.0]丁烷与α-酮酯的结构依赖性、可切换的Alder-烯反应/[2π + 2σ]环加成反应
Structure-Dependent, Switchable Alder-Ene/[2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with α-Ketoesters Enabled by Palladium Catalysis.
作者信息
Wang Wei, Xiao Jun-An, Zheng Lan, Liang Wen-Jie, Yang Liu, Huang Xiao-Xiang, Lin Chenxiang, Chen Kai, Su Wei, Yang Hua
机构信息
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, People's Republic of China.
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, People's Republic of China.
出版信息
Org Lett. 2024 Dec 13;26(49):10645-10650. doi: 10.1021/acs.orglett.4c04251. Epub 2024 Dec 4.
A structure-dependent, palladium-catalyzed switchable alder-ene/[2π + 2σ] cycloaddition of VBCBs with α-ketoesters has been reported. A variety of cyclobutenes and 2-oxabicyclo[2.1.1]hexanes have been efficiently achieved in good to excellent yields through strain-release-driven alder-ene reactions and [2π + 2σ] cycloadditions, respectively. The potential of this method is illustrated by the scale-up reaction and diverse postsynthetic transformations of the obtained cyclic scaffolds. Additionally, the reaction mechanism and origins of the chemoselectivity have been probed by computational studies.
据报道，一种结构依赖性的、钯催化的VBCB与α-酮酯的可切换烯反应/[2π + 2σ]环加成反应。通过应变释放驱动的烯反应和[2π + 2σ]环加成反应，分别以良好至优异的产率高效地实现了多种环丁烯和2-氧杂双环[2.1.1]己烷的合成。该方法的潜力通过放大反应和所得环状骨架的多种合成后转化得以体现。此外，通过计算研究对反应机理和化学选择性的起源进行了探索。
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