5-取代呋喃-2(3)-酮与 8,8-二氰基庚富烯的 [8 + 2]-环加成反应。
5-Substituted-furan-2(3)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene.
机构信息
Institute of Organic Chemistry, Department of Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Łódź, Poland.
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
出版信息
J Org Chem. 2022 Apr 15;87(8):5296-5302. doi: 10.1021/acs.joc.2c00101. Epub 2022 Mar 29.
This study demonstrates the use of organocatalytic Brønsted base activation of 5-substituted-furan-2(3)-ones to generate 2π-components for the diastereoselective [8 + 2]-cycloaddition involving 8,8-dicyanoheptafulvene as an 8π-component. The use of dienolates in a higher-order cycloaddition reaction leads to the formation of biologically relevant polycyclic products bearing a γ-butyrolactone structural motif, thus broadening the synthetic potential of Brønsted base activated higher-order cycloadditions.
本研究展示了使用有机催化的 Brønsted 碱激活 5-取代呋喃-2(3)-酮，生成 2π 组分，用于涉及 8,8-二氰基庚富烯作为 8π 组分的立体选择性 [8 + 2]-环加成。在更高阶环加成反应中使用烯醇盐会导致形成具有γ-丁内酯结构基序的生物相关的多环产物，从而拓宽了 Brønsted 碱激活的高阶环加成的合成潜力。
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