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

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Chinese Journal of Chemistry 2024年第7期42卷 699-704页

作者： Chenggui Wu Ze-Shui Liu Yong Shang Chang Liu Shuang Deng Hong-Gang Cheng Hengjiang Cong Yinchun Jiao Qianghui Zhou Sauvage Center for Molecular Sciences Engineering Research Center of Organosilicon Compounds&Materials(Ministry of Education)Hubei Key Lab on Organic and Polymeric OptoElectronic MaterialsCollege of Chemistry and Molecular SciencesThe Institute for Advanced Studiesand TaiKang Center for Life and Medical SciencesWuhan UniversityWuhanHubei 430072China Key Laboratory of Xin'an Medicine Ministry of EducationAnhui University of Chinese MedicineHefeiAnhui 230038China School of Chemistry and Chemical Engineering Hunan University of Science and TechnologyXiangtanHunan 411201China

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

asymmetric Hydrogenation of Phenanthridines with Chiral Boranes

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Chinese Journal of Chemistry 2024年第6期42卷 631-635页

作者： Guangyu Cui Xiangqing Feng Haifeng Du Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionInstitute of ChemistryChinese Academy of SciencesBeijing100190 China University of Chinese Academy of Sciences Beijing100049 China

The asymmetric hydrogenation of N-heteroarenes provides an efficient method for the synthesis of optically active cyclic secondary amines.In this paper,we described an asymmetric hydrogenation of phenanthridines using a chiral mono-alkene-derived borane.A variety of dihydrophenanthridines were furnished in high yields with up to 93%ee.The current catalytic system was very sensitive for the steric hindrance of phenanthridines.Bulky substituents at one phenyl group of phenanthridines were required to obtain the high enantioselectivity.But large substituents on the carbon of the C=N bonds would diminish the reactivity sharply.

关键词： asymmetric catalysis Hydrogenation Nitrogen heterocycles Phenanthridines Frustrated Lewis pairs Chiral boranes

Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles

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Chinese Journal of Chemistry 2024年第7期42卷 731-735页

作者： Wen Bao Ye-Hui Chen Yu-Wei Liu Shao-Hua Xiang Bin Tan School of Pharmacy&StateKey Laboratory of Applied Organic Chemistry Lanzhou UniversityLanzhouGansu 730000China Shenzhen Grubbs Institute Department of ChemistrySouthern University of Science and TechnologyShenzhenGuangdong 518055China

Indole-based atropisomers are a very important class of axially chiral compounds.However,the atroposelective synthesis of axially chiral 2-arylindole remains largely unexplored.In this study,we report the successful synthesis of atropisomeric 2-arylindoles using direct amination of indoles with p-quinonediimines in the presence of chiral phosphoric acid as a catalyst.Quinonediimine acts as an aminating reagent through formal polarity inversion of imine.The malonate group on the 2-aryl of 2-indoles was found to be essen-tial for high enantioselectivity of the products.This could be due to the additional interaction between the ester group and the cata-lyst,as well as the intramolecular hydrogen bonding.Our findings provide a new strategy for the asymmetric construction of 2-arylindole atropisomers.

关键词： Chiral phosphoric acid Quinonediimines Direct amination Nucleophilic addition asymmetric catalysis Enantioselectivity Axially chiral 2-arylindole Atroposelective synthesis

Sequential enantioselective Ugi-4CR/post-Ugi transformation strategy:a precise construction of structurally diverse azaspiro polycyclic scaffolds

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Science China Chemistry 2024年第2期67卷 576-586页

作者： Xiao-Bao Wu Jun-Xiu Shi Yi-Ming Ou Hua-Jie Jiang Yi-Jun Fang Qi-Ming Wang Quan Gao Jie Yu Department of Applied Chemistry Anhui Province Engineering Laboratory for Green Pesticide Development and ApplicationAnhui Province Key Laboratory of Crop Integrated Pest ManagementAnhui Agricultural UniversityHefei230036China

A privileged strategy has been developed for the precise construction of enantioenriched azaspiro polycyclic scaffolds.Structurally diverse azaspiro polycycles bearing multiple contiguous stereocenters are obtained with excellent results(up to 99:1 e.r.,>95:5 d.r.) via sequential enantioselective four-component Ugi reactions/post-Ugi transformations with substrates containing prerequisite functional groups in the presence of anionic stereogenic-at-cobalt(Ⅲ) complexes.

关键词： asymmetric catalysis post-Ugi transformation anionic stereogenic-at-cobalt(Ⅲ)complex azaspiro polycyclic scaffold one-pot synthesis

Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates

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Science China Chemistry 2024年第4期67卷 1175-1180页

作者： Hao-Dong Qian Xiang Li Tingrui Yin Wei-Feng Qian Chunhui Zhao Cuiju Zhu Hao Xu CCNU-uOttawa Joint Research Centre Key Laboratory of Pesticides&Chemical Biology of Ministry of EducationInternational Joint Research Center for Intelligent Biosensing Technology and HealthCollege of ChemistryCentral China Normal UniversityWuhan 430079China

Here,we describe a strategy for the copper-catalyzed asymmetric heteroarylation of yne-thiophene carbonates with indoles via remote substitution.The key to the success of this strategy lies in the design of the alkynyl group at the ortho-position of the heterocycle thiophene,enabling the formation of a triarylmethane moiety via very remote substitution.Thus,the concept of remote copper-catalyzed asymmetric transformation extends not only to yne-allylic esters but also to yne-aryl esters.The reaction readily provides a diverse array of chiral triarylmethanes with high efficiency,enantioselectivity,and excellent functional group compatibility.Moreover,facile follow-up transformations underscore their potential utility in the synthesis of various enantioenriched building blocks.Preliminary mechanistic studies support the plausibility of the remote substitution pathway.

关键词： remote substitution copper catalyst asymmetric catalysis triaryl methanes

Cobalt(Ⅲ)hydride HAT mediated enantioselective intramolecular hydroamination access to chiral pyrrolidines

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Science China Chemistry 2024年第6期67卷 2002-2008页

作者： Qi Meng Tao Qin Huanran Miao Ge Zhang Qian Zhang Jilin Province Key Laboratory of Organic Functional Molecular Design&Synthesis Department of ChemistryNortheast Normal UniversityChangchun130024China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032China

Enantioenriched pyrrolidines and derivatives are ubiquitous substructures in compounds of importance to medicinal and biological chemistry.Herein,we report an efficient cobalt-catalyzed intramolecular asymmetric hydroamination reaction that produces chiral pyrrolidines with good to excellent yield and enantiocontrol.Compared with previously reported radicalinvolved methodologies for enantioenriched pyrrolidines,these conditions feature two elegant versatilities,enabling(1)the use of cobalt-catalyzed hydrogen atom transfer(HAT)to generate organocobalt intermediates that bring radical reaction to organometallic chemistry,and(2)enantioselective intramolecular C-N bond forging through an S_(N)2-like displacement involving dynamic kinetic resolution(DKR).This approach provides a new alternative and efficient methodology for enantioselective radical-involved C-N bond construction that can be used in the synthesis of both chiral pyrrolidines and homologous nitrogen heterocycles.

关键词： asymmetric catalysis radical hydroamination cobalt catalysis hydrogen atom transfer

Recent Progress of asymmetric catalysis from a Chinese Perspective

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CCS Chemistry 2023年第12期5卷 2685-2716页

作者： Yan-Mei He Yuan-Zheng Cheng Yingdong Duan Yan-Dong Zhang Qing-Hua Fan Shu-Li You Sanzhong Luo Shou-Fei Zhu Xue-Feng Fu Qi-Lin Zhou Beijing National Laboratory for Molecular Sciences Institute of ChemistryChinese Academy of SciencesBeijing 100190 State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032 Center of Basic Molecular Science Department of ChemistryTsinghua UniversityBeijing 100084 State Key Laboratory and Institute of Elemento-Organic Chemistry College of ChemistryNankai UniversityTianjin 300071 Department of Chemical Sciences National Natural Science Foundation of ChinaBeijing 100085

The precise construction of chiral molecules is a core research area in chemical science and technology.Among the plethora of reported synthetic methods,asymmetric catalysis has emerged as one of the most efficient and direct ways to obtain optically pure chiral compounds.This article mainly reviews the recent progress of asymmetric catalysis made by Chinese chemists from the following aspects:the development of new chiral ligands,transition metal-catalyzed asymmetric reactions,asymmetric organocatalytic reactions,and new strategies for asymmetric catalysis.This review does not intend to be comprehensive;only representative examples are selected to highlight the important progress made in this field.Finally,a brief outlook is given on the development of novel chiral ligands/catalysts,new enantioselective reactions,and their applications in chiral drugs and agricultural chemicals.

关键词： asymmetric catalysis chiral ligands organocatalysts enantioselective reactions cooperative catalysis

Catalytic enantioselective N-silylation of sulfoximine

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Chinese Chemical Letters 2024年第4期35卷 352-356页

作者： Xingfen Huang Jiefeng Zhu Chuan He Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of CatalysisSouthern University of Science and TechnologyShenzhen 518055China Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal UniversityHangzhou 311121China

A rhodium/diphosphine-catalyzed asymmetric cross-dehydrogenative coupling between sulfoximines and dihydrosilanes has been achieved. This is the first report on the enantioselective N-silylation of sulfoximines. The protocol gives access to a variety of Si-stereogenic N-silylated sulfoximines in decent yield(up to 99%) with excellent stereoselectivity(up to 99%), featuring high atom economy, and a cleaner manner with H2as the sole byproduct. The obtained bis-Si-stereogenic monohydrosilane product can be further converted into the corresponding chiral polymer with pendant sulfoximine groups.

关键词： N-Silylation of sulfoximine Chiral silylamine Si-stereogenic silanes Si-CADC asymmetric catalysis

Ni-Catalyzed Enantioselective Difunctionalization of Alkynes to Azepine Derivatives Bearing a Quaternary Center and an Unprotected Imine

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Chinese Journal of Chemistry 2024年第8期42卷 873-878页

作者： Jian Long Zhiwu Lu Xiao-Lin Li Peng Xue Wen-Bo Liu Engineering Research Center of Organosilicon Compounds&Materials(Ministry of Education)and College of Chemistry and Molecular Sciences Wuhan UniversityWuhanHubei430072 China

Comprehensive Summary,The azepine ring is a prominent structural scaffold in biologically significant molecules. In this study, we present a Ni(II)-catalyzed asymmetric difunctionalization of alkynes, involving intermolecular regioselective arylation and intramolecular nitrile addition, enabling the synthesis of enantioenriched azepine derivatives. This reaction simultaneously installs an all-carbon quaternary stereocenter and introduces an unprotected imine functionality, showing great promise for subsequent transformations. The reaction exhibits good tolerance toward various functional groups, resulting in high yields and enantioselectivities. The synthetic utility of this methodology is further demonstrated through gram-scale synthesis and product derivatization. This research offers an efficient approach to the synthesis of seven-membered nitrogen heterocycles.

关键词： Nickel asymmetric catalysis N-Heterocycles Alkyne functionalization Quaternary centers