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Facile access to chiral 1-pyrrolines through Rh-catalyzed enantioselective partial hydrogenation of unprotected simple pyrroles

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Chinese Chemical Letters 2022年第12期33卷 5092-5095页

作者： Kui Tian Gongyi Liu xiu-qin dong Engineering Research Centre of Organosilicon Compounds&Materials Ministry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhan 430072China Suzhou Institute of Wuhan University Suzhou 215123China

Highly enantioselective Rh-catalyzed partial hydrogenation of unprotected simple 2-alkyl-5-aryl-disubstituted pyrroles has been successfully developed,generating a series of chiral 1-pyrroline derivatives generally with excellent results(95%-99%yields,91%-96%ee).Moreover,2,5-aryl-1H-pyrroles were hydrogenated well in high yields and good *** efficient protocol features easily accessible substrates,wide substrate scope,well functional group compatibility,commercially available rhodium precursor and chiral *** provides a versatile route to access chiral 1-pyrroline derivatives that are of great importance in organic synthesis and pharmaceutical chemistry.

关键词： Chiral 1-pyrrolines Partial hydrogenation Unprotected simple pyrroles Regioselectivity Enantioselectivity

Design, Synthesis and Application of Multifunctional Chiral Aminophosphine Catalyst for Asymmetric Intermolecular Cross Rauhut-Currier Reaction

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Chinese Journal of Chemistry 2022年第17期40卷 2061-2066页

作者： Wu-Wei dong Kui Tian xiu-qin dong Chun-Jiang Wang Engineering Research Center of Organosilicon Compounds&Materials Ministry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhanHubei430072 China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai230021 China Suzhou Institute of Wuhan University SuzhouJiangsu215123 China

A series of structurally novel multifunctional chiral aminophosphine catalysts were developed through a concise synthetic strategy from easily available starting *** highly enantioselective intermolecular cross Rauhut-Currier reactions of vinyl ketones with 3-acyl acrylates and 2-ene-1,4-diones catalyzed by(S,S)-5a were well realized,generating a wide range of the structurally important chiral multicarbonyl products in good to excellent yields with high stereocontrol(up to 97%yield,99%ee).In addition,a series of 31P NMR experiments were carried out to further investigate the catalytic process.

关键词： Asymmetric catalysis Chiral aminophosphine Intermolecular cross Rauhut-Currier reaction Chiral multicarbonyl molecules Enantioselectivity

Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation

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Chinese Chemical Letters 2020年第7期31卷 1859-1862页

作者： Lin Tao qingyang Zhao Xumu Zhang xiu-qin dong Key Laboratory of Biomedical Polymers Engineering Research Centre of Organosilicon Compounds&MaterialsMinistry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhan 430072China Department of Chemistry and Shenzhen Grubbs Institute Southern University of Science and TechnologyShenzhen 518055China School of Pharmaceutical Sciences(Shenzhen) Sun Yat-sen UniversityShenzhen 518107China

Rh/ZhaoPhos-catalyzed asymmetric hydroge nation of a series of(E)-2-(chro man-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities(up to 99%yield,98%ee).Moreover,the gram-scale hydrogenation could be performed well in the presence of 0.02 mol%catalyst loading(TON=5000),the hydrogenation product was easily converted to access other important compounds,which demonstrated the synthetic utility of this asymmetric catalytic methodology.

关键词： Chiral 4-substituted chromanes Asymmetric hydrogenation Excellent enantioselectivity Gram-scale synthesis Bisphosphine-thiourea ligand

A Computational Study of Asymmetric Hydrogenation of 2-Phenyl Acrylic Acids Catalyzed by a Rh(l) Catalyst with Ferrocenyl Chiral Bisphosphorus Ligand: The Role of Ion-Pair Interaction

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Chinese Journal of Chemistry 2021年第6期39卷 1616-1624页

作者： Xiangru Fan Lini Zheng Yuhong Yang xiu-qin dong Xumu Zhang Lung-Wa Chung Deportment of Chemistry Guangdong Provincial Key Laboratory of Catalysis and Shenzhen Grubbs InstituteSouthern University of Science and TechnologyShenzhenGuangdong 518055China Key Laboratory of Biomedical Polymers Engineering Research Center of Organosilicon Compounds&MaterialsMinistry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhanHubei 430072China

Asymmetric hydrogenation reaction is one of the most efficient synthetic methods to form useful chiral compounds for synthetic chemistry,medicinal chemistry and material ***,the enantioselectivity of many hydrogenation reactions is controlled by steric hindrance between the chiral ligand and ***,Zhang group developed a highly asymmetric hydrogenation of 2-aryl and 2-alkyl acrylic acids catalyzed by a Rh(l)catalyst with a chiral Wudaphos *** excellent enantioselectivity of this asymmetric reaction was proposed to be controlled by ion-pair interaction between the substrate and chiral *** this study,a systematic density functional theory study has been carried out to investigate the reaction mechanism and origin of the *** computational results suggest that this reaction follows the classic mechanism involving oxidative addition of H_(2),migratory insertion and reductive *** from the C=C coordination to the metal in the common oxidative addition step,our study found that the chelation of the carboxyl group of the substrate to the cationic Rh(l)metal is more favorable in this oxidative addition *** high enantioselectivity is proposed to be dictated by a better catalyst/substrate geometric complementarity in the major pathway to have less distortion of the catalyst for a strong ion-pair interaction.

关键词： Hydrogenation Enantioselectivity Reaction mechanism Density functional theory Ion-pair interaction

Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides: Efficient access to chiral pyrrolidine-3-sulfonyl fluorides

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Chinese Chemical Letters 2021年第12期32卷 4029-4032页

作者： Yi-Nan Li Xin Chang Qi Xiong xiu-qin dong Chun-Jiang Wang Engineering Research Centre of Organosilicon Compounds&Materials Ministry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhan 430072China Shanghai Institute of Organic Chemistry Chinese Academy of SciencesShanghai 200032China Suzhou Institute of Wuhan University Suzhou 215123China

Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides(ESFs) was successfully developed, this protocol provided an efficient and facile method to a wide range of chiral pyrrolidine-3-sulfonyl fluorides with good to excellent results(up to 87% yield,>20:1 dr, 94% ee). Some other chiral sulfonyl derivatives, such as sulfonamide and sulfonate, were easily accessible through simple transformations with high yields, which demonstrated that the cycloaddition products could be synthetically useful in the sulfur(VI) fluoride exchange(Su FEx) chemistry.

关键词： Chiral pyrrolidine-3-sulfonyl fluorides Asymmetric 1 3-dipolar cycloaddition Azomethine ylides Excellent stereoselectivity Sulfur(Ⅵ)fluoride exchange

Stereodivergent Synthesis of Carbocyclic Quaternary α-Amino Acid Derivatives Containing Two Contiguous Stereocenters

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Chinese Journal of Chemistry 2022年第9期40卷 1059-1065页

作者： Cong Fu Qi Xiong Lu Xiao Ling He Tian Bai Zongpeng Zhang xiu-qin dong Chun-Jiang Wang Engineering Research Center of Organosilicon Compounds&Materials Ministry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhanHubei 430072China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 230021China Suzhou Institute of Wuhan University SuzhouJiangsu 215123China

A novel approach to stereodivergent synthesis of carbocyclicα-quaternary amino acid derivatives,bearing two contiguous stereocenters,is proposed through sequential dual Cu/Ir-catalyzed asymmetric allylation and ring-closing metathesis.A variety of five and six-membered carbocyclicα-quaternary amino acid derivatives could be readily achieved in good to high yields with exclusive regioselectivities,excellent diastereoselectivities(13:1->20:1 dr)and enantioselectivities(generally>99%ee).Of particular note is that the current protocol is also a versatile synthetic tool for the stereodivergent construction of the challenging seven and eight-membered carbocyclicα-amino acid *** four stereoisomers of these important molecules could be precisely synthesized through the permutation of chiral Cu/Ir catalytic *** power of this strategy has been demonstrated for the facile access to some biologically active chiral molecules,such as spiro-hydantoins.

关键词： Asymmetric catalysis Enantioselectivity Amino acids Allylation Metathesis

Sequential Ir-Catalyzed Allylation/2-aza-Cope Rearrangement Strategy for the Construction of Chiral Homoallylic Amines

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Chinese Journal of Chemistry 2020年第8期38卷 807-811页

作者： Ruo-qing Wang Chong Shen Xiang Cheng Zuo-Fei Wang Hai-Yan Tao xiu-qin dong Chun-Jiang Wang Engineering Research Center of Organosilicon Compounds&Materials Ministry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhanHubei 430072China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 230021China

Sequential Ir-catalyzed asymmetric allylation/2-aza-Cope rearrangement of arylidene aminomalonates with allylic carbonates was successfully developed,and a variety of enantioenriched homoallylic amine derivatives were obtained in high yields with good chirality transfer and excellent E/Z-geometry control(up to 99%yield,96%ee).Compared with previous dual catalytic system established for this transformation,the current mono metal catalytic system provides a simpler and more practical protocol employing the readily available starting materials.

关键词： materials system starting

Ir-Catalyzed Asymmetric Hydrogenation of Unprotected Indoles:Scope Investigations and Mechanistic Studies

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CCS Chemistry 2023年第6期5卷 1398-1410页

作者： Gongyi Liu Lini Zheng Kui Tian Haifeng Wang Lung Wa Chung Xumu Zhang xiu-qin dong Engineering Research Center of Organosilicon Compounds and Materials Ministry of EducationCollege of Chemistry and Molecular SciencesWuhan UniversityWuhanHubei 430072 Pharmaceutical Research Institute Wuhan Institute of TechnologyWuhanHubei 430205 Department of Chemistry Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of CatalysisSouthern University of Science and TechnologyShenzhenGuangdong 518000 Suzhou Institute of Wuhan University SuzhouJiangsu 215123

Transition metal-catalyzed asymmetric hydrogenation(AH)of unprotected indoles has mainly been applied to alkyl substituted unprotected ***,the challenging aryl substituted unprotected indoles with poor reactivity and enantioselectivity(≤42%ee)could not be hydrogenated *** this work,a highly efficient Ir/bisphosphine-thiourea ligand ZhaoPhos catalytic system for the AH of challenging aryl substituted unprotected indoles has been successfully developed for the first time with high reactivity and excellent stereoselective ***,a series of 2-alkyl-substituted and 2,3-disubstituted unprotected indoles were also well tolerated in this catalytic system.A wide variety of chiral indoline derivatives were obtained in good to high yields with excellent stereoselectivities(75–99%yields,>20:1 dr,and 86–99%ee).The anion-binding activation strategy played an important role in accessing both high reactivity and excellent stereoselectivity,which was formed between the catalyst and unprotected indoles in situ-generating iminium ion with the assistance of Brønsted acid.A possible catalytic mechanism was proposed for this Ir-catalyzed AH according to density functional theory calculations and control experiment *** available substrates,a broad range of substrate tolerance,an efficient chiral catalytic system,and a gram-scale protocol further demonstrated the potential practicality of this methodology.

关键词： asymmetric hydrogenation unprotected indoles anion-binding activation strategy chiral indoline derivatives enantioselectivity

Copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides withβ-trifluoromethyl-substituted alkenyl heteroarenes

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Science China Chemistry 2023年第11期66卷 3193-3204页

作者： Xiang Cheng Xin Chang Yuhong Yang Zongpeng Zhang Jing Li Yipu Li Wenxiao Zhao Lung Wa Chung Huailong Teng xiu-qin dong Chun-Jiang Wang College of Chemistry and Molecular Sciences Wuhan UniversityWuhan 430072China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryShanghai 230021China Shenzhen Grubbs Institute Department of Chemistry and Guangdong Provincial Key Laboratory of CatalysisSouthern University of Science and TechnologyShenzhen 518055China College of Science Huazhong Agricultural UniversityWuhan 430070China

Copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides andβ-trifluoromethyl-substituted alkenyl heteroarenes was developed for the first time.A wide range of enantioenriched pyrrolidines containing both heteroarenes and trifluoromethyl group with multiple stereogenic centers could be readily accessible by this method with good to high yields and excellent levels of both stereo-and regioselectivity(up to 99%yield,>20:1 rr,>20:1 dr,and up to 95%ee).Notably,substratecontrolled umpolung-type dipolar cycloaddition was also disclosed in this protocol to achieve regiodivergent synthesis withα-aryl substituted aldimine esters as the dipole *** DFT studies were conducted to explore the origin of the stereo-and regioselectivity of this 1,3-dipolar cycloaddition,and suggest that copper(Ⅱ)salt utilized in this catalytic system could be reduced in-situ to the active copper(Ⅰ)species and might be responsible for the observed high stereo-and regioselectivity.

关键词： asymmetric catalysis 1 3-dipolar cycloaddition chiral pyrrolidines heteroarene trifluoromethyl group

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