Li Jia, Dong Ziyang, Zhai Hongxuan, Wu Jicheng, Zhao Changgui
Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China.
J Org Chem. 2024 Oct 18;89(20):15374-15379. doi: 10.1021/acs.joc.4c02021. Epub 2024 Sep 27.
Atroposelective synthesis of -disubstituted []paracyclophanes is a difficult task in organic chemistry. We describe a facile approach for the synthesis of -disubstituted []paracyclophanes using Pd-catalyzed enantioselective C-H olefination and sequential reductive cleavage. A wide range of []paracyclophanes was obtained with excellent enantioselectivity. Thermodynamic analysis revealed that the rotational barrier of -disubstituted []paracyclophanes was lower than that of -disubstituted []paracyclophanes. The synthesized planar-chiral [14]paracyclophane showed a bright fluorescence emission and impressive circularly polarized luminescence activity.
在有机化学中，对位选择性合成二取代[ ]对环芳烷是一项艰巨的任务。我们描述了一种使用钯催化的对映选择性C-H烯烃化和顺序还原裂解来合成二取代[ ]对环芳烷的简便方法。获得了一系列具有优异对映选择性的[ ]对环芳烷。热力学分析表明，二取代[ ]对环芳烷的旋转势垒低于二取代[ ]对环芳烷的旋转势垒。合成的平面手性[14]对环芳烷表现出明亮的荧光发射和令人印象深刻的圆偏振发光活性。
