Pd-catalyzed asymmetric carbonyl alkynylation:Synthesis of axial chiral ynones

作     者：Long Jin Jian Han Dongmei Fang Min Wang Jian Liao 

作者机构：Natural Products Research CenterChengdu Institute of BiologyChinese Academy of SciencesChengdu 610041China College of Chemical EngineeringSichuan UniversityChengdu 610065China University of Chinese Academy of SciencesBeijing 100049China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2024年第35卷第6期

页      面：293-297页

核心收录：

学科分类：081702[工学-化学工艺] 08[工学] 0817[工学-化学工程与技术] 0703[理学-化学] 

基　　金：supported financially by National Nature Science Foundation of China(No.22171258) the Youth Innovation Promotion Association CAS(No.2022375) the Biological Resources Programme,Chinese Academy of Sciences(No.KFJ-BRP-008) the Sichuan Science and Technology Program(No.2022ZYD0038) 

主　　题：Pd-catalyzed Axial chiral ynones Cyclic diaryliodonium High-valent palladium catalyzed Asymmetric carbonyl alkynylation 

摘      要：Ynones are important skeletons in bioactive molecules and valuable building blocks for organic synthesis,thus great efforts have been devoted to their ***,introducing prochiral substrates to construct ynones bearing a chiral framework is unrealized to ***,we reported the first example of Pd/SOP-catalyzed asymmetric carbonylative alkynylation via a non-classical carbonylative Sonogashiratype approach(acyl-Pd(Ⅱ)species generated from nucleophiles).By using cyclic diaryliodonium salts as prochiral substrates,various axial chiral ynones with good functional group tolerance(39 examples),satisfied yields(71%-96%)and excellent enantioselectivities(generally 94%-99%ee)were *** of bioactive compounds,scale-up experiment and useful transformations were also conducted to demonstrate the utility of this process.