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Enantioselective Synthesis of Benzimidazole Atropisomers Featuring a N-N Axis

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Chinese Journal of Chemistry 2024年第7期42卷 711-718页

作者： Fang-Bei Ge Qi-Kun Yin Chuan-Jun Lu Xuan Xuan Jia Feng Ren-Rong Liu College of Chemistry and Chemical Engineering Qingdao UniversityQingdaoShandong 266071China School of Pharmacy Key Laboratory of Mlecular Pharmacoogy and Drug EvaluationMinistry of EducationYantai Universit YantaiShandong 264005China

Atroposelective synthesis of N-N atropisomers is an emerging area but remains underexplored;in particular,the synthesis of N-N benzimidazole atropisomers is still unprecedented.Herein,the first enantioselective synthesis of N-N benzimidazole atropisomers via the palladium-catalyzed de novo construction of benzimidazole skeleton is presented.With readily available palladium catalyst and biphosphine ligand,a broad range of nonbiaryl benzimidazole and indole-benzimidazole atropisomers were conveniently ac-cessed in high yields and with excellent enantioselectivities.Significantly,these N-N benzimidazole atropisomers showed great anti-tumor activity and selectivity to breast cancer MCF-7 cells.The simple catalytic system,broad substrate scope,high enantioselectivi-ty,and good bioactivity make this approach highly attractive.

关键词： Asymmetric synthesis atropisomerism Palladium Benzimidazole Antitumor

Synthesis of Axially Chiral Anilides Enabled by a Palladium/Ming-Phos-Catalyzed Desymmetric Sonogashira Reaction

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Chinese Journal of Chemistry 2022年第3期40卷 317-322页

作者： Bin Yang Junfeng Yang Junliang Zhang Deportment of Chemistry Fudon University2005 Songhu RoadShanghai 200438China

Atropisomeric anilides are one of important C-N axially chiral compounds.Compared with the A/-terminal functionalization to prepare such compounds,C-terminal functionalization strategies have been rarely reported.We describe herein an efficient synthesis of axially chiral anilides enabled by Pd-catalyzed desymmetric Sonogashira cross-coupling reactions with the use of a newly identified Ming-Phos.Moderate to high yields with high enantioselectivities(up to 98%ee)were obtained.

关键词： atropisomerism Axially chiral anilides SadPhos Desymmetrization Sonogashira cross-coupling Kinetic resolution

Preparation of Optically Active 2,2'-Dibromo-6,6'-diiodo-1,1'-biphenyl:A Powerful Precursor for Modular Synthesis of Functionalized Atropisomers

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Chinese Journal of Chemistry 2023年第24期41卷 3515-3520页

作者： Yuanyuan Li Longhui Duan Biqiong Hong Zhenhua Gu Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry University of Science and Technology of China96 Jinzhai RoadHefeiAnhui230026 China College of Materials and Chemical Engineering Minjiang UniversityFuzhouFujian350108 China

The widespread applications of atropisomeric compounds have led to an increasing demand for their synthesis.Rather than synthesizing different functionalized atropisomers individually,an attractive alternative is to identify a key intermediate or precursor that can be readily elaborated and functionalized to realize divergent synthesis of this class of compounds.Building on our previous research on asymmetric ring-opening of cyclic diaryliodoniums,in this work we developed a copper-catalyzed enantioselective ring-opening reaction of ortho,ortho’-dibromo substituted cyclic diaryliodonium with lithium iodide.The resulting optically active product 2,2'-dibromo-6,6'-diiodo-1,1'-biphenyl,possessing two C—Br bonds and two C—I bonds,can be selectively advanced to form different functionalities.Remarkably,the utilities of the product were highlighted by successively demonstrating C—I and C—Br metalation,followed by carboxylation,boroylation,oxygenation,allylation,phosphinylation,etc.,all of which provide a new and convenient approach to synthesizing a range of functionalized axially chiral biphenyls.

关键词： atropisomerism Asymmetric catalysis Ring-opening reaction Chirality Copper

Atroposelective sp3 C—H Coupling for Kinetic Resolution of Thioanilide Atropisomers

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Chinese Journal of Chemistry 2021年第12期39卷 3269-3276页

作者： Hua-Jie Jiang Rui-Long Geng Jia-Hui Wei Liu-Zhu Gong Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry University of Science and Technology of ChinaHefeiAnhui 230026China Center for Excellence in Molecular Synthesis of CAS HefeiAnhui 230026China

A highly efficient kinetic resolution of racemic thioanilide atropisomers via C(sp^(3))-H arylation has been achieved by a hybrid palladium catalyst bearing an anionic chiral Co^(Ⅲ)-complex and a phosphoramidite ligand,leading to both enantioenriched atropisomeric arylation thioanilides(up to 99%ee)and N-Me atropisomeric thioanilides(up to 99%ee),simultaneously.The remained enantioenriched substrates can be arylated again by using an achiral anionic ligand to give the enantiomer with the opposite configuration.

关键词： Kinetic resolution C—H activation atropisomerism Chiral Co^(Ⅲ)-complex Phosphoramidite

Atroposelective Construction of Axially Chiral Alkene-lndole Scaffolds via Catalytic Enantioselective Addition Reaction of 3-Alkynyl-2-indolylinethanols

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Chinese Journal of Chemistry 2021年第8期39卷 2163-2171页

作者： Jing-Yi Wang Meng Sun Xian-Yang Yu Yu-Chen Zhang Wei Tan Feng Shi School of Chemistry and Materials Science Jiangsu Normal UniversityXuzhouJiangsu 221116China

Atroposelective construction of axially chiral alkene-heteroaryl scaffolds is highly desired but challenging.In this work,we established an atroposelective construction of axially chiral alkene-indole scaffolds via th... 详细信息

关键词： atropisomerism Axial chirality Asymmetric catalysis Indole Nucleophilic addition