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Construction of a Bicyclo[2.2.2]octene Skeleton via a Visible-Light-Mediated Radical Cascade Reaction of Amino Acid Derivatives with N-(2-Phenyl)benzoyl Groups
Organic Letters ( IF 4.9 ) Pub Date : 2023-06-27 , DOI: 10.1021/acs.orglett.3c01586 Yuki Yoshida 1 , Haruka Takeuchi 1 , Kohei Nakagawa 1 , Toshiki Fujii 1 , Norihito Arichi 1 , Shinya Oishi 1 , Hiroaki Ohno 1 , Shinsuke Inuki 1
Organic Letters ( IF 4.9 ) Pub Date : 2023-06-27 , DOI: 10.1021/acs.orglett.3c01586 Yuki Yoshida 1 , Haruka Takeuchi 1 , Kohei Nakagawa 1 , Toshiki Fujii 1 , Norihito Arichi 1 , Shinya Oishi 1 , Hiroaki Ohno 1 , Shinsuke Inuki 1
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Bridged polycyclic ring systems constitute the core structures of numerous natural products and biologically active molecules. We found that simple biphenyl substrates derived from amino acids participate in a radical cascade reaction under visible light irradiation in the presence of [Ir{dF(CF3)ppy}2(dtbpy)]PF6 to enable the direct construction of bicyclo[2.2.2]octene structures. Isotopic labeling experiments suggested that intramolecular hydrogen atom transfer is involved in the cascade processes.
中文翻译：
通过氨基酸衍生物与 N-(2-苯基)苯甲酰基的可见光介导的自由基级联反应构建双环[2.2.2]辛烯骨架
桥连多环系统构成了众多天然产物和生物活性分子的核心结构。我们发现，在[Ir{dF(CF 3 )ppy} 2 (dtbpy)]PF 6存在下，源自氨基酸的简单联苯底物在可见光照射下参与自由基级联反应，从而能够直接构建双环[2.2 .2]辛烯结构。同位素标记实验表明分子内氢原子转移参与级联过程。
更新日期：2023-06-27
中文翻译：
通过氨基酸衍生物与 N-(2-苯基)苯甲酰基的可见光介导的自由基级联反应构建双环[2.2.2]辛烯骨架
桥连多环系统构成了众多天然产物和生物活性分子的核心结构。我们发现，在[Ir{dF(CF 3 )ppy} 2 (dtbpy)]PF 6存在下，源自氨基酸的简单联苯底物在可见光照射下参与自由基级联反应，从而能够直接构建双环[2.2 .2]辛烯结构。同位素标记实验表明分子内氢原子转移参与级联过程。
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