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Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation ofα-dehydro amino ketones

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Science China Chemistry 2023年第10期66卷 2847-2851页

作者： Xuefeng Tan Shuang Gao Chunyan Yang Qiwei Lang Xiaobing Ding Gen-Qiang Chen Xumu Zhang Laboratory of Small Molecule Drug Discovery and Synthesis Department of ChemistrySouthern University of Science and TechnologyShenzhen 518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhen 518000China Department of Chemistry City University of Hong KongHong Kong 999077China

A series of novel atropisomeric diphosphine ligands termed Tan Phos were designed and synthesized,which has a smaller bite angle compared with that of other ligands such as BINAP.Tan Phos showed high reactivity and enantioselectivity in the rhodiumcatalyzed asymmetric hydrogenation ofα-dehydro amino ketones,and up 99%yield and 99%ee were obtained for a wide range of chiralα-amino ketones.

关键词： diphosphine asymmetric hydrogenation chiral ligand

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 indoles.However,the challenging aryl substituted unprotected indoles with poor reactivity and enantioselectivity(≤42%ee)could not be hydrogenated well.In 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 control.Moreover,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 results.Readily 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

Iridium-Catalyzed asymmetric hydrogenation of Tetrasubstituted Exocyclic Olefins:An Efficient Access to Dexmethylphenidate

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CCS Chemistry 2023年第12期5卷 2808-2817页

作者： Yingying Tian Yu-Yi Zhu Jianchao Yu Dong-Huang Liu Qin Yin Shao-Fei Ni Shao-Tao Bai Xumu Zhang Department of Chemistry Shenzhen Grubbs InstituteSouthern University of Science and TechnologyShenzhen Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou UniversityShantou Shenzhen Institute of Advanced Technology Chinese Academy of SciencesShenzhen Institute of Carbon-Neutral Technology and Center for Carbon-Neutrality Catalysis and Engineering Shenzhen Polytechnic UniversityShenzhen

An Ir-catalyzed enantioselective hydrogenation of challenging tetrasubstituted exocyclic olefins is disclosed.This new catalytic system tolerates a broad substrate scope and affords valuable chiral cyclic β-amino esters possessing two vicinal stereocenters in high yields and excellent enantioselectivities and diastereoselectivities(up to 94% yield,96% ee,99:1 dr).Control experiments and deuterium-labeling reactions reveal an iminium hydrogenation mechanism upon Brønsted acid-promoted tautomerization of the C=C double bond to cycliciminium intermediates.Density functional theory calculations showcase that the excellent selectivities are derived from C-H…π interaction between the substrate and the chiral ligand.Application in gram-scale preparation of dexmethylphenidate with up to 1500 turnover number is also demonstrated,showing the promising potential of Ir-catalyzed enantioselective hydrogenation in drug synthesis.

关键词： asymmetric hydrogenation tetrasubstituted olefins iridium Bronsted acids dexmethylphenidate

asymmetric hydrogenation of aromatic ketones using new chiral-bridged diphosphine/diamine-Ru(Ⅱ) complexes

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Chinese Chemical Letters 2010年第12期21卷 1403-1406页

作者： Yu Ming Cui Lai Lai Wang Fuk Yee Kwong Wei Sun State Key Laboratory for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical Physics Chinese Academy of Sciences Lanzhou 730000 China Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis and Department of Applied Biology and Chemical technology The Hong Kong Polytechnic University Hong Kong China Graduate University of Chinese Academy of Sciences Beijing 100039 China

A series of chiral secondary alcohols were easily prepared by means of asymmetric hydrogenation of prochiral aromatic ketones using a new（（Rax）-BuP）/（R,R）-DPEN-Ru（Ⅱ） complex catalyst system.The hydrogenation of 2-methylacetophenone in n-butanol （t-BuOK/Ru =45.6/1,S/C = 500,20 atm.of H2,20℃,48 h） afforded（S）-1-（2＇-methylphenyl）ethanol in 92%ee and〉99% conversion.

关键词： asymmetric hydrogenation Chiral alcohols Diphosphine ligand Ruthenium complexes Diamine

Unified total synthesis of eburnamine-vincamine indole alkaloids based on catalytic asymmetric hydrogenation/lactamization cascade

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Green Synthesis and Catalysis

Green Synthesis and Catalysis 2022年第3期3卷 291-293页

作者： Wen Zhang Yansong Xue Srihari Konduri Guodan Lin Mengjuan Wu Pei Tang Fener Chen Sichuan Research Center for Drug Precision Industrial Technology West China School of PharmacySichuan UniversityChengdu 610041China Engineering Center of Catalysis and Synthesis for Chiral Molecules Department of ChemistryFudan UniversityShanghai 200433China Shanghai Engineering Center of Industrial asymmetric Catalysis for Chiral Drugs Shanghai 200433China Skaggs School of Pharmacy and Pharmaceutical Science UC San Diego9500 Gilman DriveLa JollaCA 92093-0934United States

The enantioselective total synthesis of representative members of the eburnamine-vincamine alkaloids(+)-vincamine,(-)-eburnamonine,and(-)-criocerine has been accomplished.The synthesis took advantage of a highly stereoselective Ir-catalyzed hydrogenation/lactamization cascade reaction,which allows for the stereo-selective construction of the C/D rings as well as the installation of the critical cis-C20/C21 relative stereo-chemistry of the eburnamine-vincamine alkaloid skeleton in one pot.

关键词： Indole alkaloid Imine asymmetric hydrogenation Natural product Enantioselective synthesis

asymmetric hydrogenation of 2-Aryl-5,6-dihydropyrazine Derivatives with Chiral Cationic Ruthenium Diamine Catalysts

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Chinese Journal of Chemistry 2014年第10期32卷 991-994页

作者： Yong Li Yanmei He Fei Chen Qinghua Fan Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionInstitute of ChemistryChinese Academy of Sciences(CAS)Beijing 100190China Department of Chemistry Henan Institute of EducationZhengzhouHenan 450046China Collaborative Innovation Center of Chemical Science and Engineering TianjinChina

The first asymmetric hydrogenation of unfunctionalized 2-substituted and 2,3-disubstituted 5,6-dihydropyrazines catalyzed by chiral cationic Ru-diamine complex(R,R)-1a was developed,affording chiral piperazine derivat... 详细信息

关键词： asymmetric hydrogenation ruthenium chiral diamines piperazines

Efficient P-Chiral Biaryl Bisphosphorus Ligands for Palladium-Catalyzed asymmetric hydrogenation

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Chinese Journal of Chemistry 2018年第2期36卷 153-156页

作者： Wenhao Jiang Qing Zhao Wenjun Tang Department of Pharmaceutical Engineerin& School of Pharmacy East China University of Science and Technology 130 Meilong Rd Shanghai 200037 China State Key Laboratory of Bio-Organic and Natural Products Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling RdShanghai 200032

A series of structurally novel P-chiral biaryl bisphosphorus ligands L1-L5 （BABIBOPs） are developed, providing high efficiency for the first time in palladium-catalyzed asymmetric hydrogenation of β-aryl and β-alkyl substituted β-keto esters. With the Pd-1.3 （iPr-BABIBOP） catalyst, a series of chiral β-hydroxyl carboxylic esters are formed in excellent enantioselectivities （up to 〉 99% ee） and yields at catalyst loading as low as 0.01 mol%.

关键词： biaryl bisphosphorus ligands asymmetric hydrogenation enantioselectivity palladium P-chiral

Synthesis of Chiral α-Benzyl-β^(2)-hydroxy Carboxylic Acids through Iridium-Catalyzed asymmetric hydrogenation of α-Oxymethylcinnamic Acids

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Chinese Journal of Chemistry 2014年第8期32卷 783-787页

作者： Ze-Yu Li Song Song Shou-Fei Zhu Na Guo Li-Xin Wang Qi-Lin Zhou State Key Laboratory and Institute of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China Collaborative Innovation Center of Chemical Science and Engineering(Tianjin)

An asymmetric hydrogenation of α-oxymethylcinnamic acids was developed by using chiral spiro phosphineoxazoline/iridium complexes as catalysts to prepare β^(2)-hydroxycarboxylic acids with high reactivity(TON up to 2000)and excellent enantioselectivity(up to 99.5%ee).By using this highly efficient asymmetric hydrogenation as a key step,a concise total synthesis of natural product homoisoflavone(S)-(+)-4 was accomplished.

关键词： asymmetric hydrogenation chiral spiro ligands iridium catalysts α-oxymethylcinnamic acids α-benzyl-β^(2)-hydroxy carboxylic acids

Ir-Catalyzed asymmetric hydrogenation of α-Alkylidene β-Lactams and Cyclobutanones

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Chinese Journal of Chemistry 2018年第7期36卷 612-618页

作者： Jingzhao Xia Yu Nie Guoqiang Yang Yangang Liu Ilya D. Gridnev Wanbin Zhang Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Pharmacy Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China School of Chemistry and Chemical Engineering Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China Department of Chemistry Graduate School of Science Tohoku University Aramaki 3-6 Aoba-ku Sendai 9808578 Japan

Chiral β-Iactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stereocontrolled construction of four-membered ring （mini-sized） β-lactams and cyclobutanones via an Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation, providing the corresponding optically active four-membered ring carbonyl products bearing an α-chiral carbon center with excellent yields （up to 99%） and enantioselectivities （up to 98%） under mild reaction conditions （1.0-2.5 bar H2 for 1.0-10 h）. The reaction presents wide substrate scope. Diverse transformations of the catalyzed products were also conducted to show the potential utility of this protocol.

关键词： β-lactam cyclobutanone iridium phosphine-oxazoline ligand asymmetric hydrogenation