- 作 者: ( "wanbin zhang" OR "wan-bin zhang" )
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Pd-Catalyzed Asymmetric Allylic Substitution Cascade of Substituted 4-Hydroxy-2H-pyrones with meso-Allyl DicarbonatesOrganic Letters (IF 6.005) Pub Date : 2022-05-11 ,DOI:10.1021/acs.orglett.2c00937Yan Zheng, Siqi Dong, Kai Xu, Delong Liu, Wanbin ZhangAn efficient Pd-catalyzed asymmetric allylic substitution cascade of 4-hydroxy-2H-pyrones with meso-allyl dicarbonates has been developed for the synthesis of kinetic chiral tetrahydro-1H-pyrano[4,3-b]benzofuran-1-one products in ≤87% yield and ≤99% ee. The protocol was achieved via a temperature-controlled kinetic control process, which has been illustrated by means of the experimental results and ...
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Two-pack frequency-selective incoherent holography by using a dual-beam setupOptics and Lasers in Engineering (IF 4.836) Pub Date : 2022-05-04 ,DOI:10.1016/j.optlaseng.2022.107086Wanbin Zhang, Baosheng Li, Chunlin Shi, Jianquan LiWe proposed a new incoherent optical frequency selection method called two-pack frequency-selective (TPFS) incoherent holography, which compresses two on-axis holograms into a single multiplexed on-axis hologram without loss of magnification and resolution. The spectrum we want to reconstruct is intercepted by multiple confounding correlation terms in the spatial frequency domain. The background bias ...
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Synthesis and evaluation of a multi-block polycarboxylic acid for improving low-rank coal to make the slurryColloids and Surfaces A: Physicochemical and Engineering Aspects (IF 4.539) Pub Date : 2022-04-12 ,DOI:10.1016/j.colsurfa.2022.128966Junfeng Zhu, Jinling Li, Ruiqing Liu, Junqi Wang, Yiwen Tang, Wanbin Zhang, Guanghua ZhangTo increase the solid concentration and optimize the rheological properties and of low-rank coal water slurry (CWS), a series of multi-block polycarboxylic acid (PCRaf) dispersants wearing hybrid-length side chains by the reversible addition-fragmentation chain transfer (RAFT) polymerization in aqueous solution. Meantime, the random polycarboxylic acid (PCRan) dispersants with same monomers were prepared ...
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Stereodivergent Desymmetrization of Simple Dicarboxylates via Branch-Selective Pd/Cu Catalyzed Allylic Substitution.Chemistry (Weinheim an der Bergstrasse, Germany) Pub Date : 2022-03-24 ,DOI:10.1002/chem.202200273Guanlin Li,Ling Zhao,Yicong Luo,Youbin Peng,Kai Xu,Xiaohong Huo,Wanbin ZhangAsymmetric desymmetrization has been demonstrated to be a powerful strategy for building stereocenters in asymmetric synthesis. Herein, a Pd/Cu catalyzed asymmetric desymmetrization reaction with a simple geminal dicarboxylate is reported. A wide scope of imino esters bearing an aryl or heteroaromatic group were compatible with this bimetallic catalytic system. The reactions proceeded smoothly, giving ...
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RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolutionChemical Communications (IF 6.222) Pub Date : 2022-03-23 ,DOI:10.1039/d2cc01193jJingjing Li, Jianxun Ye, Jiayu Zhou, Jing Li, Delong Liu, Wanbin ZhangThe efficient RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolution has been achieved for the synthesis of chiral tetrahydronaphthols. The mechanism study indicated that hydrogenation with H2 gas, rather than transfer hydrogenation with EtOH solvent as the hydrogen source, predominates in the reaction pathway. ...
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Nickel/Copper-Cocatalyzed Asymmetric Benzylation of Aldimine Esters for the Enantioselective Synthesis of α-Quaternary Amino AcidsAngewandte Chemie International Edition (IF 15.336) Pub Date : 2022-03-23 ,DOI:10.1002/anie.202203448Youbin Peng, Chongyu Han, Yicong Luo, Guanlin Li, Xiaohong Huo, Wanbin ZhangThe first Ni/Cu cocatalyzed asymmetric benzylation of aldimine esters has been developed. DFT calculations revealed that the strong electrophilicity of the η3-benzylnickel intermediate enabled the reaction to proceed smoothly under base-free conditions. The method was applied to the synthesis of BIRT-377 analogues, the key intermediate of PD154075 and CI-988. ...
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Copper-Catalyzed Regioselective [3+3] Annulations of Alkynyl Ketimines with α-Cyano Ketones: the Synthesis of Polysubstituted 4H-Pyran Derivatives with a CF3 -Containing Quaternary Center.Chemistry (Weinheim an der Bergstrasse, Germany) Pub Date : 2022-03-18 ,DOI:10.1002/chem.202200128Cheng Sheng,Zheng Ling,Tanveer Ahmad,Fang Xie,Wanbin ZhangRegioselective [3+3] annulation of alkynyl ketimines with α-cyano ketones for the synthesis of polysubstituted 4H-pyran derivatives with a quaternary CF3 -containing center has been realized by using Cu(OAc)2 as the catalyst. The novel strategy tolerates a wide range of α-CF3 alkynyl ketimines and α-cyano ketones with both aryl and alkyl substitutents. A preliminary asymmetric synthesis of chiral product ...
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Hyperbranched ionic surfactants with polyether skeleton: Synthesis, properties and used as stabilizer for emulsion polymerizationJournal of Molecular Liquids (IF 6.165) Pub Date : 2022-03-16 ,DOI:10.1016/j.molliq.2022.118937Wanbin Zhang, Yanmeng Wang, Shaowu Wang, Zehua Guo, Ce Zhang, Xiuzhong Zhu, Guanghua ZhangA versatile strategy involves anionic ring-opening polymerization (AROP) and thiol-ene reaction was contributed for the construction of hyperbranched ionic surfactants. A series of hyperbranched surfactants composed of polyether skeleton and various ionic side groups such as anion, cation and zwitterion were synthesized and labeled as HPEanionic, HPEcationic and HPEzwitterionic, respectively. The chemical ...
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Stereodivergent Desymmetrization of Simple Dicarboxylates via Branch-Selective Pd/Cu Catalyzed Allylic SubstitutionChemistry - A European Journal (IF 5.236) Pub Date : 2022-03-09 ,DOI:10.1002/chem.202200273Guanlin Li, Ling Zhao, Yicong Luo, Youbin Peng, Kai Xu, Xiaohong Huo, Wanbin ZhangA Pd/Cu catalyzed stereodivergent desymmetrization of unsubstituted allylic dicarboxylates was developed and the corresponding products could be generated in excellent yields with good stereoselectivity. Notably, the reaction favored branch-selectivity. Large scale experiment and the transformations of products indicated the potential utility of this reaction. In addition, computational studies revealed ...
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Copper-Catalyzed Regioselective [3+3] Annulations of Alkynyl Ketimines with α-Cyano Ketones: the Synthesis of Polysubstituted 4H-Pyran Derivatives with a CF3-Containing Quaternary CenterChemistry - A European Journal (IF 5.236) Pub Date : 2022-02-28 ,DOI:10.1002/chem.202200128Cheng Sheng, Zheng Ling, Tanveer Ahmad, Fang Xie, Wanbin ZhangA regioselective [3+3] annulation of alkynyl ketimines with α-cyano ketones for the synthesis of polysubstituted 4H-pyran derivatives with a quaternary CF3-containing center has been realized by using Cu(OAc)2 as a catalyst, providing the desired products in up to 99 % yield. The method tolerates some variations in the α-CF3 alkynyl ketimines and α-cyano ketones scope. The products could be synthesized ...
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Three-dimensional high-precision assessment of mountainous urban underground space resources: A case study in Chongqing, ChinaTunnelling and Underground Space Technology (IF 5.915) Pub Date : 2022-02-28 ,DOI:10.1016/j.tust.2022.104439Yue Xi, Xiaojun Li, Hehua Zhu, Wanbin Zhang, Sicheng Zhao, Wenyun XuUrban underground space resource (UUSR) assessment can facilitate the planning of underground space development and utilization in highly populated urban areas. Typically, UUSR assessment involves dividing the assessment area, determining the assessment index, establishing the assessment model, integrating the assessment data, and calculating the results. A method for streamlining the three-dimensional ...
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Cu-catalyzed asymmetric addition of alcohols to β,γ-alkynyl-α-imino esters for the construction of linear chiral N,O-ketalsNature Communications (IF 14.919) Pub Date : 2022-01-20 ,DOI:10.1038/s41467-022-28002-7Cheng Sheng, Zheng Ling, Yicong Luo, Wanbin ZhangShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.
N,O-acetals are part of many synthetic intermediates and important skeletons of numerous natural products and pharmaceutical drugs. The most straightforward method of the synthesis of N,O-acetals is the enantioselective addition of O-nucleophiles to imines. However, using this method for the synthesis of linear chiral N,O-ketals still remains challenging due to the instability of raw materials under
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Synthesis of Chiral Hydantoins and Thiazolidinediones via Iridium‐Catalyzed Asymmetric HydrogenationChinese Journal of Chemistry (IF 6.0) Pub Date : 2022-01-03 ,DOI:10.1002/cjoc.202100809Yu Nie, Jing Li, Qianjia Yuan, Wanbin ZhangHerein, we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand. The transformation shows good functional group tolerance, and gives the hydrogenated products with excellent yields (up to 99%) and enantioselectivities (up to 98% ee). A gram-scale reaction was also carried out, and provided the hydrogenated ...
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Quantum beetle swarm algorithm optimized extreme learning machine for intrusion detectionQuantum Information Processing (IF 2.349) Pub Date : 2021-12-23 ,DOI:10.1007/s11128-021-03311-wDong, Yumin, Hu, Wanbin, Zhang, Jinlei, Chen, Min, Liao, Wei, Chen, ZhengquanBecause of the low accuracy in intrusion detection, a model of extreme learning machine based on the optimization of quantum beetle swarm algorithm is proposed. First of all, this paper proposes a quantum beetle swarm optimization algorithm, which introduces quantum mechanics and combines the advantages of beetle antennae search and particle swarm optimization. In this way, the individual can learn ...
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Chemical Synthesis of the Anti-COVID-19 Drug Remdesivir.Current protocols Pub Date : 2021-12-01 ,DOI:10.1002/cpz1.303Mo Wang,Lu Zhang,Xiaohong Huo,Zhenfeng Zhang,Wanbin Zhang
Remdesivir has become an important compound for the treatment of COVID-19. Here, we describe the catalytic asymmetric synthesis of this anti-COVID-19 drug. First, the P-racemic phosphoryl chloride is synthesized in a facile procedure. Then, it is possible to obtain the protected remdesivir via the organocatalytic asymmetric phosphorylation of protected nucleoside GS441524 with P-racemic phosphoryl
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Comparison of ester-based slow-release polycarboxylate superplasticizers with their polycarboxylate counterpartsColloids and Surfaces A: Physicochemical and Engineering Aspects (IF 4.539) Pub Date : 2021-11-13 ,DOI:10.1016/j.colsurfa.2021.127878Pengchao Feng, Guanghua Zhang, Wanbin Zhang, Hongyue Cui, Tong XinEster-based slow-release polycarboxylate superplasticizers (PCT) exhibit high fluidity and a good slump retention effect on concrete slurries. Hence, in this study, a previously prepared unsaturated triethyl citrate (as the functional monomer) and acrylic acid and isoprenyloxy polyethylene glycol (as the primary raw materials) were employed to synthesize a series of PCT via free-radical polymerization ...
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Pd(II)-Catalyzed Enantioselective Ring-Contraction for the Construction of 1,4-BenzoxazinesThe Journal of Organic Chemistry (IF 4.354) Pub Date : 2021-11-02 ,DOI:10.1021/acs.joc.1c01874Chenghao Ye, Feng Gao, Haipeng Wei, Jianzhong Chen, Guoqiang Yang, Qianjia Yuan, Wanbin ZhangEnantioselective ring-contraction reactions have not been widely reported. We have developed an enantioselective ring contraction of 5,6-dihydro-2H-benzo[b][1,4]oxazocines, affording enantiomerically enriched 3,4-dihydro-2H-1,4-benzoxazine derivatives as single regioisomers. An acidic additive is necessary in order to obtain the products with good yields and enantiomeric ratios (up to 93% yield, 98:2 ...
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Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholinesChemical Science (IF 9.825) Pub Date : 2021-10-28 ,DOI:10.1039/d1sc04288bMingxu Li, Jian Zhang, Yashi Zou, Fengfan Zhou, Zhenfeng Zhang, Wanbin Zhang
Asymmetric hydrogenation of unsaturated morpholines has been developed by using a bisphosphine-rhodium catalyst bearing a large bite angle. With this approach, a variety of 2-substituted chiral morpholines could be obtained in quantitative yields and with excellent enantioselectivities (up to 99% ee). The hydrogenated products could be transformed into key intermediates for bioactive compounds.
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Study on the preparation and performance comparison of side-chain hydroxyl-terminated polybutadiene derivatives with narrowly molecular weight distribution used for polyurethanePolymer Testing (IF 4.282) Pub Date : 2021-10-26 ,DOI:10.1016/j.polymertesting.2021.107389Lingxiao Ma, Xiuzhong Zhu, Wanbin Zhang, Haitao Zhang, Jianyong Wang, Jianbo Qu
Hydroxy-terminated oligomers with narrow molecular weight distribution using as soft segment of polyurethane can significantly increase the modulus, tensile strength, and elongation at break of the polyurethane. Thus, design and synthesis of new hydroxy-terminated oligomers having narrow molecular weight distribution can improve the properties of polyurethane and further expand the use range of polyurethane
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Kinetic resolution of azaflavanones via a RuPHOX-Ru catalyzed asymmetric hydrogenationOrganic Chemistry Frontiers (IF 5.281) Pub Date : 2021-10-08 ,DOI:10.1039/d1qo01310fYue Zhu, Jiayu Zhou, Jing Li, Kai Xu, Jianxun Ye, Yufei Lu, Delong Liu, Wanbin ZhangThe kinetic resolution of azaflavanones has been established via RuPHOX-Ru catalyzed asymmetric hydrogenation, providing chiral azaflavanones and azaflavanols in high yields with up to >20 : 1 dr and 99.7% ee. The highly efficient kinetic resolution process has been illustrated based on the deuterium labelling and racemization experiments. The reaction could be performed on a gram-scale with a relatively ...
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Rhodium-Catalyzed Asymmetric Hydrogenation of 3-Benzoylaminocoumarins for the Synthesis of Chiral 3-Amino DihydrocoumarinsAngewandte Chemie International Edition (IF 15.336) Pub Date : 2021-10-01 ,DOI:10.1002/anie.202110286Yunnan Xu, Delong Liu, Yu Deng, Yi Zhou, Wanbin ZhangAn asymmetric hydrogenation of 3-benzoylaminocoumarins was achieved for the first time using our BridgePhos-Rh catalytic system, providing chiral 3-amino dihydrocoumarins in high yields (up to 98 %) and with excellent enantioselectivities (up to 99.7 % ee). The relationship between the enantioselectivities of the hydrogenations and the dihedral angles and the resulting π-π stacking effects of the BridgePhos-Rh ...
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Upgrade of low rank coal by using emulsified asphalt and its application for preparation of coal water slurry with high concentrationJournal of Dispersion Science and Technology (IF 2.262) Pub Date : 2021-09-23 ,DOI:10.1080/01932691.2021.1979998Lun Du, Guanghua Zhang, Shining Hu, Jie Luo, Wanbin Zhang, Ce Zhang, Junguo Li, Junfeng ZhuAbstract The hydrophilic surface and developed pore structure restricted the application of abundant low rank coals (LRC) for the preparation of coal water slurry (CWS) with high concentration. In this work, emulsified asphalt was applied as an effective and low cost modifier to modify coal surface and improve the slurry making performance of LRC. The successful modification was verified by various ...
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Enantio- and Diastereodivergent Synthesis of Spirocycles through Dual-Metal-Catalyzed [3+2] Annulation of 2-Vinyloxiranes with Nucleophilic DipolesAngewandte Chemie International Edition (IF 15.336) Pub Date : 2021-09-16 ,DOI:10.1002/anie.202111842Youbin Peng, Xiaohong Huo, Yicong Luo, Liang Wu, Wanbin ZhangA dual-metal-catalyzed asymmetric [3+2] annulation of 2-vinyloxiranes with the challenging nucleophilic dipoles (imino esters) was achieved. It was successfully applied to the stereodivergent synthesis of structurally rigid spirocyclic framework. A series of spiro compounds bearing a pyrroline and an olefin were synthesized in an enantio- and diastereodivergent manner. ...
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Enantio- and Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu CatalysisJournal of the American Chemical Society (IF 15.419) Pub Date : 2021-08-05 ,DOI:10.1021/jacs.1c05087Jiacheng Zhang, Xiaohong Huo, Junzhe Xiao, Ling Zhao, Shengming Ma, Wanbin ZhangIn contrast to the widely explored methods for the asymmetric synthesis of molecules bearing a single stereocenter or adjacent stereocenters, the concurrent construction of 1,3-stereogenic centers in an enantio- and diastereoselective manner remains a challenge, especially in acyclic systems. Herein, we report an enantio- and diastereodivergent construction of 1,3-nonadjacent stereocenters bearing ...
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Asymmetric hydrogenation of γ-branched allylamines for the efficient synthesis of γ-chirogenic aminesNatural Sciences Pub Date : 2021-08-05 ,DOI:10.1002/ntls.10021Jian Zhang, Tiantian Chen, Yuanhao Wang, Fengfan Zhou, Zhenfeng Zhang, Ilya D. Gridnev, Wanbin Zhang
The efficient construction of γ-chirogenic amines has been realized via asymmetric hydrogenation of γ-branched N-phthaloyl allylamines by using a bisphosphine-Rh catalyst bearing a large bite angle. The desired products possessing different γ-substituents were obtained in quantitative yields and with excellent enantioselectivities (up to >99% ee). This protocol provides a practical method for the preparation
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Synthesis of Chiral 2-Substituted 1,4-Benzoxazin-3-ones via Iridium-Catalyzed Enantioselective Hydrogenation of BenzoxazinonesOrganic Letters (IF 6.005) Pub Date : 2021-07-02 ,DOI:10.1021/acs.orglett.1c01701Yu Nie, Jing Li, Jun Yan, Qianjia Yuan, Wanbin ZhangAn efficient iridium-catalyzed enantioselective hydrogenation of 2-alkylidene 1,4-benzoxazin-3-ones using our developed iPr-BiphPHOX as a ligand is reported. This method showed good functional group compatibility and delivered the corresponding reduced products in excellent yields (up to 99%) with excellent enantioselectivities (up to 99% ee). The reaction proceeded very well on a gram scale with low ...
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Nickel-Catalyzed Asymmetric Hydrogenation of HydrazonesEuropean Journal of Organic Chemistry (IF 3.021) Pub Date : 2021-06-04 ,DOI:10.1002/ejoc.202100642Bowen Li, Dan Liu, Yanhua Hu, Jianzhong Chen, Zhenfeng Zhang, Wanbin ZhangAn asymmetric hydrogenation of hydrazones with a unique nickel catalyst has been developed for the synthesis of chiral hydrazines with up to 99 % yield and 99.4 : 0.6 er and a broad substrate scope. Deuterium labelling experiments indicated that the hydrazone substrates undergo imine-enamine tautomerization in the mixed solvents. ...
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Cobalt-Catalyzed Chemo- and Enantioselective Hydrogenation of Conjugated EnynesAngewandte Chemie International Edition (IF 15.336) Pub Date : 2021-06-01 ,DOI:10.1002/anie.202106566Yanhua Hu, Zhenfeng Zhang, Yangang Liu, Wanbin ZhangAsymmetric hydrogenation is one of the most powerful methods for the preparation of single enantiomer compounds. However, the chemo- and enantioselective hydrogenation of the relatively inert unsaturated group in substrates possessing multiple unsaturated bonds remains a challenge. We herein report a protocol for the highly chemo- and enantioselective hydrogenation of conjugated enynes while keeping ...
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Hydroxyl-terminated Polyethylenes Bearing Functional Side Groups: Facile Synthesis and Their PropertiesChinese Journal of Polymer Science (IF 3.603) Pub Date : 2021-05-31 ,DOI:10.1007/s10118-021-2572-5Wan-Bin Zhang, Jie Luo, Yan-Meng Wang, Xiu-Zhong Zhu, Ce Zhang, Jing Liu, Mei-Le Ni, Guang-Hua ZhangA series of hydroxyl-terminated polyethylenes (HTPE) bearing various functional side groups (e.g. carboxyl, ester and butane groups) were synthesized by the combination of ring-opening metathesis polymerization (ROMP) and visible light photocatalytic thiol-ene reaction. The products are named as α, ω-dihydroxyl-poly[(propionyloxythio)methinetrimethylene] (HTPEcarboxyl), α, ω-dihydroxyl-poly[(methylpropionatethio) ...
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Mechanistic Study of Ni and Cu Dual Catalyst for Asymmetric C–C Bond Formation; Asymmetric Coupling of 1,3-Dienes with C-nucleophiles to Construct Vicinal StereocentersACS Catalysis (IF 13.084) Pub Date : 2021-05-21 ,DOI:10.1021/acscatal.1c01626Jingzhao Xia, Takahiro Hirai, Shoichiro Katayama, Haruki Nagae, Wanbin Zhang, Kazushi MashimaWe report details of the reaction mechanism for a coupling reaction of 1,3-dienes with C-nucleophiles that was catalyzed by a Ni/Cu cooperative catalyst system using Ni(cod)2 and [Cu(CH3CN)4]PF6 in the presence of a chiral JOSIPHOS-type bisphosphine ligand and iPr2NEt, providing direct access to highly valuable vicinal quaternary and tertiary stereocenters with high enantio- and diastereoselectivity ...
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