Ke Miaolin, Zheng Jinying, Zong Jiayi, Tang Keshuang, Wang Jiahao, Zheng Guohui, Zhang Boxuan, Cheng Dang, Ju Zhiran, Chen Fener
Institute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology 18 Chaowang Road, Gongshu District Hangzhou City Zhejiang Province China
College of Chemical Engineering, Zhejiang University of Technology 18 Chaowang Road, Gongshu District Hangzhou City Zhejiang Province China.
Chem Sci. 2025 Apr 8;16(18):8108-8113. doi: 10.1039/d5sc01050k. eCollection 2025 May 7.
An effective method for the synthesis of dihydropyrans through synergistic palladium and chiral phosphonic acid catalysis was reported. This protocol proceeded under mild reactions and provided dihydropyrans in up to 87% yield and up to 97% ee. Meanwhile, various derivations such as oxidation, Wittig-reaction, reductions, nucleophilic substitution, and Baeyer-Villiger were accomplished to furnish interesting compounds. To gain insight into the reaction mechanism, nonlinear relationship experiments and Hammett plot experiments were carried out. In addition, a range of products (3i, 4b, 4f, 4g, and 4j) accessible from this method exhibit various anti-inflammatory activities on NO and ROS inhibition.
报道了一种通过钯和手性膦酸协同催化合成二氢吡喃的有效方法。该方案在温和的反应条件下进行，以高达87%的产率和高达97%的对映体过量提供二氢吡喃。同时，还完成了各种衍生反应，如氧化、维蒂希反应、还原、亲核取代和拜耳-维利格反应，以制备有趣的化合物。为了深入了解反应机理，进行了非线性关系实验和哈米特图实验。此外，通过该方法可获得的一系列产物（3i、4b、4f、4g和4j）对一氧化氮和活性氧的抑制表现出各种抗炎活性。
