Highly Diastereo-and Enantioselective Synthesis of Quinuclidine Derivatives by an Iridium-Catalyzed Intramolecular Allylic Dearomatization Reaction  

作　　者：Lin Huang Yue Cai Hui-Jun Zhang Chao Zheng Li-Xin Dai Shu-Li You 

机构地区：[1]State Key Laboratory of Organometallic Chemistry,Center for Excellence in Molecular Synthesis,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,Shanghai 200032,China [2]Collaborative Innovation Center of Chemical Science and Engineering,Tianjin,China

出　　处：《CCS Chemistry》2019年第1期106-116,共11页中国化学会会刊（英文）

摘　　要：Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction.The catalytic system,derived from[Ir(cod)Cl]2 and the Feringa ligand,tolerates a broad range of substrates.A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields(68%–96%),diastereoselectivity(up to>20/1 dr),and enantioselectivity(up to>99%ee).These pro-ducts feature versatile functional group diversity and can undergo diverse transformations.A model that accounts for the origin of the stereoselectivity has been proposed based on density functional theory(DFT)calculations.

关 键 词：asymmetric catalysis DEAROMATIZATION INDOLE IRIDIUM 

分 类 号：O62[理学—有机化学]