Article
Chemistry, Physical
William R. R. Cassels, Evan T. T. Crawford, Jeffrey S. S. Johnson
Summary: We report a simple catalytic crystallization-driven enantio- and diastereoselective Mannich reaction for the synthesis of stereodefined alpha-monosubstituted-ss-ketoesters, dissymmetric ss-diesters, dissymmetric ss-diketones, and ss-keto amides. This method efficiently leverages product epimerization in solution. Mechanistic studies suggest that the initial enantioselective, diastereodivergent skeletal assembly is catalyzed by a chiral tertiary amine organocatalyst, followed by crystallization-induced diastereoconvergence to provide the challenging alpha-stereocenter in excellent stereoselectivity.
Article
Chemistry, Physical
Jeffrey S. Johnson, William R. Cassels, Evan T. Crawford
Summary: A simple catalytic crystallization-driven enantio- and diastereoselective Mannich reaction was disclosed for the synthesis of stereodefined alpha-monosubstituted-keto esters, dissymmetric diesters, dissymmetric diketones, and keto amides that productively leveraged product epimerization in solution. Mechanistic studies suggested that the initial enantioselective, diastereodivergent skeletal assembly was catalyzed by a chiral tertiary amine organocatalyst, which then facilitated second stage crystallization-induced diastereoconvergence to provide the challenging alpha-stereocenter in excellent stereoselectivity.
Article
Chemistry, Multidisciplinary
Jun-Hao Zhang, Hui Xu, Xiaodong Tang, Yanfeng Dang, Fa-Guang Zhang, Jun-An Ma
Summary: In this study, the efficient and stereoselective hydrogenation of congested tetra-substituted cyclic beta-enamido phosphonates/phosphine oxides was achieved using a commercially available Rh-Josiphos system. This method enables the synthesis of chiral beta-amino phosphorus compounds with two vicinal stereocenters. The protocol is applicable to various ring systems and different phosphonate/phosphine oxide groups, and it has been successfully applied to the preparation of amino-phosphine ligands. The DFT mechanistic explorations suggest that the C=C migratory insertion into the Rh-III-H bond is the rate- and stereo-determining step, and the origins of stereoselectivity are regulated by dispersion interactions and steric repulsions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Antoine d'Aleman, Oscar Gayraud, Catherine Fressigne, Emilie Petit, Laetitia Bailly, Jacques Maddaluno, Michael De Paolis
Summary: The lactonization of 2-(2-nitrophenyl)-1,3-cyclohexanediones containing an alcohol side chain and up to three distant prochiral elements is achieved through isomerization mediated by simple organocatalysts such as quinidine. This reaction produces strained nonalactones and decalactone with up to three stereocenters in high er and dr (up to 99 : 1) through a process of ring expansion. Various distant groups, including alkyl, aryl, carboxylate, and carboxamide moieties, were investigated.
Article
Chemistry, Organic
Xiaosa Lu, Jie Zhu, Yinhua Huang
Summary: A rhodium-catalyzed highly enantio- and diaster-eoselective alkenylation reaction of Ay-unsaturated butenolides is reported. The use of a chiral diene ligand enables the synthesis of chiral butyrolactones in high yields with extremely high enantioselectivities and high diastereoselectivities. The key process involves the isomerization of butenolides and subsequent dynamic kinetic resolution.
Article
Chemistry, Multidisciplinary
Chao Che, Yi-Nan Lu, Chun-Jiang Wang
Summary: A novel strategy for catalytic asymmetric synthesis of enantioenriched 3-cis- and 3-trans-substituted prolines has been successfully developed via a unique cascade radical addition/cyclization enabled by synergistic photoredox/Bronsted acid catalysis and subsequent base-assisted epimerization. This method provides a de novo access to all four stereoisomers of 3-substituted prolines, which cannot be readily obtained using current established methods. The methodology can also be extended to the asymmetric synthesis of the full complement of stereoisomers of 3-substituted pipecolinic acids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Andrea Chaves-Pouso, Andres M. Alvarez-Constantino, Martin Fananas-Mastral
Summary: Allylic gem-dichlorides can be efficient substrates for catalytic asymmetric allylboration of alkynes. The method generates chiral skipped dienes with excellent levels of chemo-, regio- enantio- and diastereoselectivity, making them versatile building blocks for the synthesis of optically active compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Cheng Sheng, Zheng Ling, Junzhe Xiao, Kai Yang, Xie Fang, Shengming Ma, Wanbin Zhang
Summary: In this study, enantio- and diastereoselective α-additions of 1-alkynyl ketimines with dual-copper-catalysis were successfully achieved under mild conditions, leading to the synthesis of chiral tetrasubstituted α-amino allenoates bearing a vicinal all-carbon quaternary stereocenter in high yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >20:1 dr). The stereodivergent synthesis of the products was realized by the asymmetric α-addition reaction and the Grignard reagent promoted epimerization. Importantly, the reaction could be smoothly scaled up and applied to introduce chiral tetrasubstituted allenyl moieties into bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Andrea Chaves-Pouso, Andres M. Alvarez-Constantino, Martin Fananas-Mastral
Summary: In this Communication, Martin Fananas-Mastral et al. report an enantio- and diastereoselective copper-catalyzed allylboration of alkynes with allylic gem-dichlorides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jian Chen, Lifu Wu, Yue Zhao, Shaolin Zhu
Summary: In this study, we report a catalytic reaction that can control two stereocenters simultaneously. By using a chiral catalyst, we achieved simultaneous control of the stereocenters in two substrates, resulting in the formation of high-value products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Esteban Matador, Javier Iglesias-Siguenza, David Monge, Pedro Merino, Rosario Fernandez, Jose M. Lassaletta
Summary: A highly enantio- and diastereoselective thiourea-catalyzed dearomatization of isoquinolines has been developed using N-tert-butylhydrazones as key neutral reagents, leading to the formation of appealing dihydroisoquinoline derivatives with excellent stereocontrol. Experimental and computational data support the generation of highly ordered complexes that play a crucial role in the selective and high-yielding transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Minami Otsubo, Kousuke Sakimoto, Hiromichi Egami, Yoshitaka Hamashima
Summary: In this study, enantio- and diastereoselective fluorination of naphthoresorcinol and resorcinol derivatives was achieved for the first time using a dicarboxylate phase-transfer catalyst. The chiral catalyst showed good efficiency and selectivity in the reactions, providing difluorination products preferentially.
Article
Chemistry, Applied
Byungjun Kim, Sukwoo Lee, Sarah Yunmi Lee
Summary: In this study, a new method was reported to successfully promote the catalytic asymmetric Diels-Alder reactions using a chiral catalyst in conjunction with a chiral isothiourea catalyst or a Bronsted acid, resulting in the synthesis of densely functionalized cyclohexenes with multiple stereocenters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Santosh K. Pagire, Naoya Kumagai, Masakatsu Shibasaki
Summary: The catalytic asymmetric cyclopropanation of alpha,beta-unsaturated amides with stabilized sulfur ylides has been successfully achieved with high yields and selectivities, providing a new synthetic route for cyclopropanes.
Article
Chemistry, Multidisciplinary
Jingdong Wang, Yuxin Liu, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Hai-feng Duan
Summary: A series of chiral thiourea compounds with multiple H-bond donors derived from hydroquinine have been reported. The aza-Henry reaction of isatin-derived ketimines and long-chain nitro-alkanes catalyzed by these chiral thioureas shows high enantioselectivity and excellent diastereoselectivity. This work represents the first report on long-chain nitroalkanes as substrates with excellent diastereoselectivity in metal-free catalytic systems.
Article
Chemistry, Organic
Shuo Liu, Jingdong Wang, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Summary: An asymmetric synthesis method for N,N'-ketal compounds derived from isatin-derived ketimines and aryl amines has been developed using an inexpensive and readily available L-tert-leucine derived urea catalyst, resulting in high yields with high enantioselectivities.
Article
Chemistry, Organic
Jing Li, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Summary: A highly enantioselective aza-Friedel-Crafts reaction of 1H-indoles with isatin-derived N-Cbz-ketimines catalyzed by quinine-derived phase-transfer catalysts was developed. Chiral 3-aminobisindole compounds containing a tetrasubstituted stereocenter were constructed in high yields (82-91%) and moderate to excellent enantioselectivities (46-94% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ji-Ming Xi, Yun-Hai Sun, Wen-Cheng Li, Yu-Heng Wu, Zhong-Lin Wei, Wei-Wei Liao
Summary: A copper-catalyzed alkene-trifluoromethylation-triggered nitrile insertion/remote functionalization relay process has been developed, which involves the generation of iminyl radical intermediates through interrupted remote 1,n-difunctionalizations of alkenes with nitrite insertion, followed by subsequent 1,n-HAT to achieve remote functionalization. This relay protocol provides a straightforward approach for the assembly of structurally diverse trifluoromethylated azaheterocycles.
Article
Chemistry, Organic
Xin Zhang, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Summary: In this study, a chiral urea catalyst derived from quinine was used to catalyze the asymmetric Mannich reaction of 3-fluorooxindoles and alpha-amidosulfones. The reaction yielded alpha-fluoro-beta-amino-oxindoles with a tertiary carbon stereocenter in high yields (up to 95%) and exhibited high enantioselectivity (95%) and diastereoselectivity (>99:1). These alpha-fluoro-beta-amino-oxindole compounds are potential candidates in the field of medicine.
Article
Chemistry, Physical
Jingyao Li, Yanhua Song, Zhonglin Wei, Fangke Wang, Xiaozhen Zhang, Haiyuan Zhu, Shihou Sheng, Haifeng Zou
Summary: Yolk-shell TiO2@void@TiO2:Eu3+ materials were successfully synthesized by sacrificial template method and their photoluminescence and photocatalytic properties were investigated. The sample calcined at 800 degrees C exhibited the strongest red emission, and the sample calcined at 900 degrees C showed the highest photocatalytic efficiency for tetracycline. The photocatalytic kinetics provided new insights into the photocatalysis mechanism and the rapid tetracycline photodegradation by the yolk shell material offered new strategies for water purification.
APPLIED CATALYSIS A-GENERAL
(2023)
Article
Chemistry, Organic
Yun-Hai Sun, Cheng-Jing Li, Ji-Ming Xi, Zhong-Lin Wei, Wei-Wei Liao
Summary: An electrochemical three-component transformation was developed for the synthesis of sulfonylated fused sultams using N-cyanamide alkene, Na2S2O5, and sulfonyl hydrazide. The reaction proceeds in an undivided electrolysis cell without a supporting electrolyte, utilizing cost-effective and easy-to-handle sodium metabisulfite as a SO2 surrogate. This sustainable and modular approach allows for the efficient construction of cyclic sulphonamides with a broad substrate scope and available reaction components.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Lili Cui, Jungang Cao, Shihui Jiao, Guangsheng Pang, Zhonglin Wei
Summary: A selective extraction process using a mixed extractant of D2EHPA and TBP was proposed to recover vanadium (IV) over chromium. Factors such as pH value, leach solution concentration, D2EHPA concentration, phase ratio, extraction time, and temperature were investigated for their influence on V and Cr separation. The optimum conditions achieved vanadium extraction above 94.0% and vanadium stripping above 93.0%. The regeneration and reusability of the organic phases were discussed, and a three-stage extraction and stripping strategy resulted in minimal vanadium loss and high purity. Precipitation efficiency reached 99.93% under the optimal conditions.
SOLVENT EXTRACTION AND ION EXCHANGE
(2023)
Article
Chemistry, Analytical
Qibo Yan, Ming Li, Yanxin Zhang, Hailong Liu, Feng Liu, Weiwei Liao, Yingwu Wang, Haifeng Duan, Zhonglin Wei
Summary: Chemical cross-linking mass spectrometry (XL-MS) is significant in analyzing protein structures and protein-protein interactions. A bifunctional cross-linker, named DBMT, has been designed and characterized to expand the application of XL-MS approach. DBMT can selectively target tyrosine and histidine residues in proteins through electrochemical click reaction and photocatalytic reaction, respectively. A novel cross-linking strategy based on DBMT has been developed and demonstrated using model proteins, which provides a comprehensive XL-MS tool for analyzing protein structure, protein complexes, protein-protein interactions, and even protein dynamics.
Article
Chemistry, Organic
Jiwei Liu, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Summary: An enantioselective Mannich reaction between N-Boc aminosulfones and 3-methylbenzofuran-2(3H)-ones, catalyzed by a quinine-derived bifunctional phase transfer catalyst, was developed. This reaction afforded a series of chiral benzofuranones with adjacent quaternary and tertiary carbon centers in high yields (up to 96%) and exhibited good diastereoselectivities (up to >99:1) and enantioselectivities (up to 98%).
Article
Materials Science, Multidisciplinary
Xue Liu, Jingwei Li, Yuan Luo, Jianjun Li, Zhonglin Wei, Jungang Cao, Haibao Lu, Dongxing Zhang
Summary: We synthesized carbon nanotubes by cross-linking citric acid with amino urea or ethylenediamine. Factors affecting the yield of carbon nanotube were optimized and the catalytic effect of hydrated metal nitrate on carbon nanotube growth was investigated. The results showed that carbon nanotube can grow in a wide range of urea content, and even a two-dimensional sheet assembled by the prepared carbon nanotubes was observed when ethylenediamine was used. This competitive strategy is believed to expand the techniques for efficient, large-scale, and low-cost synthesis of carbon nanotubes.
Article
Chemistry, Organic
Jiwei Liu, Meiyan Zhao, Shangzhi Wang, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Summary: An enantioselective Michael addition reaction of 3-methylbenzofuran-2(3H)-ones to azadienes catalyzed by an L-tert-leucine derived squaramide catalyst was developed, resulting in the synthesis of a variety of benzofuranones with adjacent quaternary and tertiary carbon centers in high yields, moderate to excellent diastereoselectivities, and enantioselectivities.
Article
Chemistry, Organic
Zhi-Hua Yan, Wen-Cheng Li, Yu-Heng Wu, Qi-Bo Yan, Zhong-Lin Wei, Wei-Wei Liao
Summary: An electrochemical trifluoromethylative cyclization of N-cyanamide alkenes and alkynes is reported, in which commercially available CF3SO2Na and readily available starting materials were used to assemble (bis)-C,N-trifluoromethylated cyclic amidines through a novel electrochemical and sustainable process. The reaction also provided a controllable access to trifluoromethylated azines and amides. Mechanism investigation and DFT calculations revealed the possible reaction pathway.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Materials Science, Multidisciplinary
Cheng Liu, Kaiqi Ye, Zhonglin Wei, Jiang Peng, Huan Xiao, Jingbo Sun, Ran Lu
Summary: A series of derivatives were synthesized through the Knoevenagel condensation reaction, and these molecular crystals exhibited significant photomechanical motions under UV irradiation. The rapid photoactuation induced by subtle photoisomerization might originate from the relatively large change in molecular width and strong intermolecular interactions. These crystals also showed photomechanical effects in water, suggesting their potential as actuators in various practical applications.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Chemistry, Multidisciplinary
Xinyan Lv, Zhonglin Wei, Canyu Cui, Wenwen Wang, Yumei Tan, Shihui Jiao, Guangsheng Pang
Summary: In this work, superhydrophobic Fe3O4@C microspheres were successfully anchored on a polyurethane (PU) sponge skeleton surface using polyvinylidene fluoride (PVDF) as an intermediate layer. The resulting Fe3O4@C/PVDF/PU sponge showed outstanding superhydrophobic performance, excellent chemical, thermal and mechanical stabilities, high separation efficiencies for surfactant-stabilized organic solvent/water emulsions, and preferable recyclability. This material holds promise for the treatment of industrial oily wastewater.
MATERIALS CHEMISTRY FRONTIERS
(2022)
