检索结果-南通市图书馆

Chinese Chemical Letters 2024年第1期35卷 222-226页

作者： Chen Chen Jin Zhou Jing Jiang Yang Li Ting Mao Cheng Peng Gu Zhan Wei Huang State Key Laboratory of Southwestern Chinese Medicine Resources School of PharmacyChengdu University of Traditional Chinese MedicineChengdu 611137China

The scope of stereochemistry recognition usually occurs near the chiral scaffold of a ligand or catalyst.Remote stereocontrol,which can surpass the limits of stereorecognition of remote prochiral centers,has long been a challenging object of great interest in asymmetric catalysis.The current work realized the remote stereocontrol of 1,7-zwitterion intermediates formed from Huang's o-amino aryl MBH carbonates.With simple and easily accessibleβ-ICD as the bifunctional catalyst,multifunctionalized tetrahydroquinoline derivatives could be synthesized via(4+2)cycloadditions with excellent enantioselectivity and diastereoselectivity under mild conditions.The strategy possesses broad substrate scope,and three types of electron-deficient enones are successfully applied.Mechanistic studies disclosed the Lewis base-catalyzed reaction pathway,and H-bonding between the catalyst and enones is crucial for long-range stereocontrol.Scale-up reaction and transformations of the tetrahydroquinoline products demonstrated the potential of this strategy.

关键词： asymmetric synthesis Tetrahydroquinoline Remote stereocontrol Pyrazolone Lewis base catalysis 1,7-Zwitterion

Enantioselective synthesis of Benzimidazole Atropisomers Featuring a N-N Axis

在线全文

学校读者我要写书评

暂无评论

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

asymmetric synthesis of bedaquiline based on bimetallic activation and non-covalent interaction promotion strategies

维普期刊数据库评论

在线全文

维普期刊数据库

学校读者我要写书评

暂无评论

Science China Chemistry 2022年第10期65卷 1968-1977页

作者： Feng Gao Jing Li Tanveer Ahmad Yicong Luo Zhenfeng Zhang Qianjia Yuan Xiaohong Huo Tao Song Wanbin Zhang Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontiers Science Center for Transformative MoleculesSchool of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China School of Pharmacy Shanghai Jiao Tong UniversityShanghai 200240China

Bedaquiline(BDQ),approved by Food and Drug Administration(FDA)in 2012 as the first anti-tuberculosis-specific drug in the last 40 years,is viewed as one of the world’s most promising treatments for tuberculosis(TB).Due to the stereoselective construction of the Csp^(3)–Csp^(3)bond with vicinal stereocenters of BDQ and its analogues being an unsolved challenge,there have not been any reports concerning its asymmetric synthesis for the current industrial production process until now.Herein,we have successfully developed a cooperative bimetallic system for the asymmetric synthesis of BDQ under the guidance of density functional theory(DFT)computations.Based on the optimized conditions,BDQ could be synthesized with excellent enantioselectivity(>99%ee)and diastereoselectivity(16:1 dr).A 5-g scale reaction was also conducted with comparably excellent results,showing its potential for industrial application.

关键词： asymmetric synthesis bedaquiline bimetallic system industrial synthetic process DFT computation

asymmetric synthesis of Anti-tuberculosis-specific Drug TBAJ-876 through Synergistic Li/Li Catalysis

在线全文

学校读者我要写书评

暂无评论

Chinese Journal of Chemistry 2023年第11期41卷 1319-1326页

作者： Jing Li Feng Gao Tanveer Ahmad Yicong Luo Zhenfeng Zhang Qianjia Yuan Wanbin Zhang Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of PharmacyShanghai Jiao Tong University800 Dongchuan RoadShanghai200240 China Frontiers Science Centre for Transformative Molecules School of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai200240 China

TBAJ-876, developed by TB Alliance, a novel anti-tuberculosis-specific drug, has entered Phase II clinical trials. Herein, the first asymmetric synthesis of TBAJ-876 has been realized using synergistic Li/Li catalysis with excellent yield of 95% and 88 : 12 er (99.6 : 0.4 er, 10 : 1 dr after simple recrystallization). Furthermore, DFT calculations and 7Li-NMR analysis illustrated the mechanism of the synergistic reaction: a chiral Li-complex activates the nucleophile to control the stereoselectivity, while the other achiral Li-complex activates the electrophile to catalyze the carbonyl addition reaction. Additionally, this protocol has been successfully carried out at 5 gram-scale, showing its industrial potential.

关键词： asymmetric synthesis TBAJ-876 Synergistic Li Li catalysis DFT calculations Noncovalent interactions Coordination modes Lithium Enantioselectivity

synthesis of Planar-Chiral[2.2]Paracyclophane-Based Oxazole-Pyrimidine Ligands and Application in Nickel-Catalyzed 1,2-Reduction ofα,β-Unsaturated Ketones

维普期刊数据库评论

在线全文

维普期刊数据库

学校读者我要写书评

暂无评论

Chinese Journal of Chemistry 2024年第7期42卷 705-710页

作者： Juan Wang Qing-Xian Xie Xiang Li Chang-Bin Yu Yong-Gui Zhou School of Chemistry Dalian University of Technology2 Linggong RoadDalianLiaoning 116024China State Key Laboratory of Catalysis Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalianLiaoning 116023China

The planar-chiral ligands have been widely applied as a class of unique and significant ligands in asymmetric catalysis.Among them,chiral[2.2]paracycyclophane has emerged as a privileged type of planar-chiral framework and has been utilized as an important toolbox due to their structural stability.Herein,we design and synthesize[2.2]paracyclophane-derived oxazole-pyrimidine ligands(abberviated as PYMCOX).These N,N-ligands with stable properties,rigid structure and large steric hindrance performed successfully in nickel-catalyzed asymmetric 1,2-reduction ofα,β-unsaturated ketones,affording the chiral allylic alcohols with up to 99%yield and 99%ee.Meanwhile,this reduction reaction could be conducted on gram-scale without loss of activity and enantioselectivity,and the chiral ligand could be conveniently recovered with high yield.

关键词： Oxazole-pyrimidine ligands Planar chirality Nickel Hydroboration asymmetric synthesis

Catalytic asymmetric synthesis of chiral azo compounds via interrupted Japp-Klingemann reaction with aryldiazonium salts

维普期刊数据库评论

在线全文

维普期刊数据库

学校读者我要写书评

暂无评论

Science China Chemistry 2022年第3期65卷 546-553页

作者： Yan Wang Aying Yihuo Lifeng Wang Shunxi Dong Xiaoming Feng Key Laboratory of Green Chemistry&Technology Ministry of EducationCollege of ChemistrySichuan UniversityChengdu 610064China

asymmetric synthesis of enantioenriched azo compounds bearing tetrasubstituted stereocenter was achieved through chiral N,N′-dioxide/metal Lewis acid promoted interrupted Japp-Klingemann reaction of aryldiazonium tetrafluoroborate salts with nucleophiles under mild conditions. This protocol features wide substrate scope and good functional group compatibility.Azaarene-containing chiral azo compounds were stable enough in Japp-Klingemann reaction condition. The key to success of the reaction was the employment of metal salt/N,N′-dioxide ligand and the dual-task roles of the base. Moreover, the X-ray crystal structure of Ni(II)/N,N′-dioxide/substrate complex confirmed that the substrate was activated by bidentate coordination, which shed light on the origin of chiral control of the reaction.

关键词： asymmetric synthesis Japp-Klingemann reaction chiral azo compounds aryldiazonium salts N-electrophile

Catalytic asymmetric synthesis of 1,4-enynes

在线全文

学校读者我要写书评

暂无评论

中国化学快报:英文版 2023年第8期34卷 18-27页

作者： Han-Yu Lu Zhi-Tao He CAS Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesShanghai 200032China School of Physical Science and Technology ShanghaiTech UniversityShanghai 201210China School of Chemistry and Materials Science Hangzhou Institute for Advanced StudyUniversity of Chinese Academy of SciencesHangzhou 310024China

1,4-Enyne units are ubiquitous skeletons in biologically active molecules and natural products.Especially,they represent versatile building blocks for abundant downstream derivatizations via controllable modifications of both alkene and alkyne units independently.Recently,great efforts have been made to establish efficient protocols to achieve optically active 1,4-enynes.Considering the enormous application potential of enantioenriched 1,4-enyne units but no related review on this topic has been described,here we aim to provide a comprehensive summary on the catalytic methods established for enantioselective constructions of these intriguing skeletons.According to the reaction types,this review is divided into five parts,including asymmetric allylic substitution,asymmetric propargylic substitution,asymmetric alkynylallylic substitution,asymmetric hydroalkynylation and asymmetric 1,2-addition of alkynes to conjugated imines or ketones.

关键词： 1,4-Enynes Catalytic reaction asymmetric synthesis

asymmetric synthesis of some new tetrahydroisoquinolinium salts

在线全文

学校读者我要写书评

暂无评论

Chinese Journal of Chemistry 1998年第2期16卷 162-170页

作者：尤启冬 Department of Medicinal Chemistry China Pharmaceutical UniversityNanjing Jiangsu 210009China

Several new tetrahydroisoquinolinium salts, analogues of atracurium, were designed and synthesized. These compounds were prepared from optically pure tetrahydropapaverine and hexamethylene diglycidate.

关键词： Tetrahydrooisoquinolinium salt neuromuscular blocking agent asymmetric synthesis

asymmetric synthesis of (-)-(2R,3R,6S)-Irnigaine

在线全文

学校读者我要写书评

暂无评论

Chinese Journal of Chemistry 2003年第10期21卷 1356-1359页

作者：马楠马大为 Department of Chemistry State Key Laboratory of Bioorganic and Natural Products Chemistry

asymmetric synthesis of irnigaine was achieved starting from an enantiopure β amino ester 5 using the condensation of amino alcohol 2 with acetylacetone and the subsequent intramolecular cyclization as the key s... 详细信息

关键词： asymmetric synthesis βamino ester piperidine condensation

Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline

在线全文

学校读者我要写书评

暂无评论

Chinese Chemical Letters 2024年第4期35卷 99-105页

作者： Tao Yu Vadim A.Soloshonok Zhekai Xiao Hong Liu Jiang Wang State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China School of Pharmacy University of Chinese Academy of SciencesBeijing 100049China Department of Organic Chemistry Ⅰ Faculty of ChemistryUniversity of the Basque Country UPV/EHUSan Sebastian 20018Spain IKERBASQUE Basque Foundation for ScienceBilbao 48013Spain School of Pharmaceutical Science and Technology Hangzhou Institute for Advanced StudyUCASHangzhou 310024China Lingang Laboratory Shanghai 200031China

Schiff base metal complexes are of great importance in pharmaceutical science owing to their unique chemical properties, which enable them to exhibit diverse biological activities such as anti-bacterial,anti-oxidant, anti-inflammatory, and anti-tumor properties. Furthermore, Schiff base metal complexes can serve as reagents and catalysts in chemical reactions. This review aims to provide an overview of our recently published studies on Cu(Ⅱ) and Pd(Ⅱ) complexes derived from proline Schiff base ligands. We also discuss the potential applications of these metal complexes in the fields of antibacterial and chiral resolution.

关键词： Schiff bases Biological activity Tailor-made amino acids asymmetric synthesis Chiral tridentate ligands Square-planar Cu(Ⅱ)-complexes Square-planar Pd(Ⅱ)-complexes