Asymmetric Two-Component Alkenyl Catellani Reaction for the Construction of C—N Axial Chirality  

作　　者：Chenggui Wu Ze-Shui Liu Yong Shang Chang Liu Shuang Deng Hong-Gang Cheng Hengjiang Cong Yinchun Jiao Qianghui Zhou 

机构地区：[1]Sauvage Center for Molecular Sciences,Engineering Research Center of Organosilicon Compounds&Materials(Ministry of Education),Hubei Key Lab on Organic and Polymeric OptoElectronic Materials,College of Chemistry and Molecular Sciences,The Institute for Advanced Studies,and TaiKang Center for Life and Medical Sciences,Wuhan University,Wuhan,Hubei 430072,China [2]Key Laboratory of Xin'an Medicine,Ministry of Education,Anhui University of Chinese Medicine,Hefei,Anhui 230038,China [3]School of Chemistry and Chemical Engineering,Hunan University of Science and Technology,Xiangtan,Hunan 411201,China

出　　处：《Chinese Journal of Chemistry》2024年第7期699-704,共6页中国化学（英文版）

摘　　要：Herein,we report an asymmetric two-component alkenyl Catellani reaction for the construction of C—N axial chirality through a palladium/chiral norbornene cooperative catalysis and an axial-to-axial chirality transfer process.Various partially aromatic iodinated 2-pyridones,quinolones,coumarin and uracil substrates react with 2,6-disubstituted aryl bromides with a tethered amide group,to afford a wide variety of polycyclic C—N atropisomers(38 examples,up to 97%e.e.).The obtained C—N axial chirality originates from the preformed transient C—C axial chirality with high fidelity.The synthetic utility of this chemistry is demonstrated by facile prepa-ration of complex quinoline and pyridine based C—N atropisomers through a N-deprotection and aromatization sequence.In addi-tion,a remote axial-to-central diastereoinduction process dictated by C—N axial chirality is observed with excellent diastereocontrol.

关 键 词：Alkenyl Catellani reaction Asymmetric catalysis ATROPISOMERISM Axial-to-axial chirality transfer HETEROCYCLES 

分 类 号：O62[理学—有机化学]