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

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

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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.

Alkenyl Catellani reactionAsymmetric catalysisAtropisomerismAxial-to-axial chirality transferHeterocycles

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

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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

Key Laboratory of Xin'an Medicine,Ministry of Education,Anhui University of Chinese Medicine,Hefei,Anhui 230038,China

School of Chemistry and Chemical Engineering,Hunan University of Science and Technology,Xiangtan,Hunan 411201,China

startup funding from Wuhan UniversityNatural Science Foundation of Anhui University of Chinese MedicineNatural Science Foundation of Anhui University of Chinese MedicineNatural Science Foundation of Anhui University of Chinese Medicine

2021rczd0032021zrzd022022AH050440

2024

10.1002/cjoc.202300621

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(7)
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