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