Article
Chemistry, Organic
Erick Martinez-Toto, Mario Ordonez, Juan C. Morales-Solis, Marcos Flores-Alamo
Summary: The diastereoselective synthesis of (2S,5R)-5-methyl-5-(phosphono)-proline, a phosphoproline derivative from L-pyroglutamic acid, is reported. The key feature of this method is the use of chiral cyclic imines as intermediates and the selective nucleophilic addition of phosphites. The target compound is obtained through cleavage and hydrolysis reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chao Shan, Jinping Xu, Liming Cao, Chaoming Liang, Ruihua Cheng, Xiantong Yao, Maolin Sun, Jinxing Ye
Summary: This study developed a practical continuous flow protocol for efficient synthesis of various functionalized piperidines within minutes, with high yields and enantiomeric excess. The scalability and utility of the process were demonstrated through the efficient synthesis of a drug precursor.
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, Organic
Gangarajulu Kesavulu, Biguvu Balachandra, Kavirayani R. Prasad
Summary: The use of lithio tris(methylthio)methane as an anion equivalent enables the synthesis of α-amino acids. Reactions with nonracemic sulfinimines yield α-sulfinamido trithioformates with excellent diastereoselectivity. Conversion of trithioformates to diverse functionalities such as α-amino acid thioesters, esters, anilides, amides, and di/tripeptides is achieved without epimerization of chiral centers.
Article
Chemistry, Organic
Siwei Wang, Chaochao Xie, Yu Zhu, Guofu Zi, Zhanbin Zhang, Guohua Hou
Summary: An efficient Ni-(S,S)-Ph-BPE complex has been developed for the asymmetric hydrogenation of cyclic N-acyl hydrazones, leading to the formation of various chiral cyclic hydrazines with high yields and enantioselectivities of over 99%. The hydrogenation reaction can proceed smoothly on a gram scale with low catalyst loading (S/C = 3000) without a decrease in enantioselectivity, and it can be applied to the asymmetric synthesis of a RIP-1 kinase inhibitor.
Article
Biochemical Research Methods
Jing-Jing Zhang, Si-Ying Wang, Hai-Tao Dai, Hai-Chao Li, Yong Wang
Summary: Chiral recognition is an emerging field in modern chemical analysis. This study focuses on the development of a cellulose derivative, cellulose-tris(4-methylphenylcarbamate) (CMPC), for chiral recognition and separation. A CMPC-functionalized extended-gate organic field effect transistor (EG-OFET) was constructed and effectively detected three chiral molecules. The study further explores the enantiomer discrimination mechanism of CMPC using spectroscopy and nuclear magnetic resonance.
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kazuki Ishizaki, Daisuke Takagi, Toru Asahi, Masahiro Kuramochi, Takuya Taniguchi
Summary: This study investigates the structural and mechanical differences between chiral and racemic crystals of two analogous molecules. The molecular and crystal structures of the analogues were compared with known chiral-racemic crystal pairs. The Young's moduli of the crystals show that racemic crystals have larger values and their thermal response agrees with the temperature dependence of lattice dynamics.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Multidisciplinary
Yue Wang, Er-Qing Li, Zheng Duan
Summary: The development of stereodivergent strategies in asymmetric synthesis is crucial for accessing the full range of stereoisomers in products with multiple stereocenters. In this study, a novel P-chirogenic ligand, YuePhos, was developed to achieve precise switching of product stereochemistry in a Pd-catalyzed asymmetric cycloaddition reaction. The method provides an efficient route for the synthesis of pyrrolidines with up to three adjacent stereocenters, with excellent enantiomeric excesses.
Article
Chemistry, Analytical
Fudan Feng, Siyun Zhang, Lei Yang, Guang Li, Weiwei Xu, Haonan Qu, Jin Zhang, Manivannan Kalavathi Dhinakaran, Chuanlai Xu, Jing Cheng, Haibing Li
Summary: The study focuses on developing a high-enantioselective microchannel membrane by incorporating chiral gold nanoparticles. The results show improved enantioselectivity, making it advantageous for chiral separation compared to nanochannel membranes reported in the literature.
ANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Miaolin Ke, Yuyan Yu, Longwu Sun, Xinzhi Li, Qianqian Cao, Xiao Xiao, Fener Chen
Summary: A synergistic palladium/copper catalysis for the asymmetric allylic alkylation of vinylethylene carbonates with aldimine esters has been developed for the synthesis of alpha-quaternary (Z)-trisubstituted allylic amino acids under mild conditions. This methodology demonstrates broad substrate compatibility with yields up to 87% and up to 94% ee. The facile scale-up and straightforward conversion to 1,2,3,5-tetrasubstituted pyrrole and 1,2,5,6-tetrahydropyridine bearing chiral quaternary carbon centers confirm the synthetic utility of this method.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Philip J. Chevis, Thanika Promchai, Christopher Richardson, Thunwadee Limtharakul, Stephen G. Pyne
Summary: A highly diastereoselective method for the synthesis of syn-beta-amino alcohols and enantioenriched anti-beta-amino alcohols has been developed using different chiral reagents, expanding the application range of existing methods.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Donggeon Nam, Antonio Tinoco, Zhuofan Shen, Ronald D. Adukure, Gopeekrishnan Sreenilayam, Sagar D. Khare, Rudi Fasan
Summary: This study presents a biocatalytic strategy utilizing engineered variants of cytochrome c(552) to synthesize enantioenriched alpha-trifluoromethyl amines with high yield and enantioselectivity. The methodology can be applied to a broad range of substrates, providing a chemoenzymatic access to valuable compounds for medicinal chemistry and the synthesis of bioactive molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Bing-Bing Wu, Jie Xu, Kang-Jie Bian, Qian Gao, Xi-Sheng Wang
Summary: Fluorinated motifs are commonly found in drugs and agrochemicals, and incorporating these motifs in drug candidates has emerged as a powerful tool in pharmaceutical research. In this study, a nickel-catalyzed asymmetric trifluoroalkylation reaction was developed for the synthesis of chiral alcohols bearing β-CF3-substituted stereogenic carbons, with high yields and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Applied
Hao-Qiang Cao, Jun-Kuan Li, Fa-Guang Zhang, Dominique Cahard, Jun-An Ma
Summary: This review comprehensively summarizes modern synthetic methods towards asymmetric construction of chiral amino carboxylic-phosphonic acid derivatives, including phosphono-containing amino acid derivatives and catalytic enantioselective synthesis as a potent strategy. Topics such as chiral resolution protocols, chiral auxiliary-directed syntheses, and valorization of abundant chiral amino acid resources are also discussed.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Kai-Kai Wang, Yan-Li Li, Shuai Xiao-Qian, Rongxiang Chen, Aili Sun, Zhan-Yong Wang
Summary: A general approach for the synthesis of substituted pyrrolidines bearing a quaternary carbon center via [3 + 2] cycloaddition between nonstabilized azomethine ylides and cyanosulfones has been developed. This efficient method provides high yields (up to 98%) and excellent diastereoselectivities (up to >25:1 dr) under ambient reaction conditions.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dawei Zhang, Xing Gao, Qiao-Qiao Min, Yucheng Gu, Guillaume Berthon, Xingang Zhang
Summary: A nickel-catalyzed cross-coupling reaction of heteroaryl halides with chlorodifluoroacetamides and chlorodifluoroacetate has been developed, which offers an efficient and potential method for synthesizing medicinal compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Xiao-Tian Feng, Jin-Xiu Ren, Xing Gao, Qiao-Qiao Min, Xingang Zhang
Summary: We developed a new practical and stable difluoroalkylating reagent that can introduce the difluoromethylene group into organic molecules under mild reaction conditions via copper catalysis. The method exhibits high selectivity and efficiency and can be used for the synthesis of various complex analogs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Yun-Ze Li, Na Rao, Lun An, Xiao-Long Wan, Yanxia Zhang, Xingang Zhang
Summary: The authors report a nickel-catalyzed enantioselective dicarbofunctionalization reaction of 3,3,3-trifluoropropene, which overcomes side reactions and provides a convenient method for the synthesis of chiral trifluoromethylated compounds.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Minqi Zhou, Zhang Feng, Xingang Zhang
Summary: The site-selective modification of amino acids, peptides, and proteins has been an important topic in organic synthesis, medicinal chemistry, and chemical biology. The introduction of fluorine functionalities into these compounds has been a useful approach to alter their properties. Direct fluorination/fluoroalkylation of proteins has gained attention due to the unique properties of fluorine, and recent advances in the synthesis of fluorinated amino acids and peptides have been summarized in this article. Two strategies, based on fluorinated building blocks and direct fluorination/fluoroalkylation, have been discussed, providing powerful tools for selective access to fluorinated amino acids, peptides, and proteins.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Kexin Wang, Qiuzi Li, Yufeng Fan, Pingping Fang, Haibing Zhou, Jian Huang
Summary: Abnormal glycometabolism has become a fundamental research topic in tumor biology due to the poor metabolic conditions promoting the emergence of the Warburg effect (WE) phenotype. This study investigated the potential of Oxabicycloheptene sulfonate (OBHS), a selective estrogen receptor modulator, in targeting breast cancer glycometabolism. The results revealed that OBHS inhibits the expression of glucose transporter 1 (GLUT1) via the PI3K/Akt signaling pathway, leading to the suppression of breast cancer progression and proliferation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Xin Zeng, Yao Li, Qiao-Qiao Min, Xiao-Song Xue, Xingang Zhang
Summary: The use of metal catalysts in controlling the reactivity of carbenes is widely used in organic synthesis, but the transfer of difluorocarbenes remains a challenge. In this study, isolable copper(I) difluorocarbene complexes were developed and used as catalysts for difluorocarbene transfer reactions. This strategy allows for the modular synthesis of organofluorine compounds and provides access to a variety of difluoromethylene-containing products. Mechanistic studies reveal a nucleophilic addition mechanism involving electrophilic copper(I) difluorocarbenes.
Article
Chemistry, Physical
Na Rao, Yun-Ze Li, Yun-Cheng Luo, Yanxia Zhang, Xingang Zhang
Summary: The nickel-catalyzed multicomponent dicarbofunctionalization of alkenes is a convenient method for synthesizing complex organofluorine compounds, but the catalytic carbofluoroalkylation of electron-deficient alkenes is still underdeveloped. In this study, a nickel-catalyzed three-component aryldifluoroalkylation reaction was reported, which involves the reaction of industry-relevant acrylonitrile and acrylate with arylboronic acids and difluoroalkyl halides. The reaction can be extended to a four-component nickel-catalyzed carbonylation reaction. This modular catalytic synthesis offers synthetic convenience, high functional group tolerance, and the ability to construct complex difluoroalkylated compounds efficiently. The utility of this synthesis has also been demonstrated by transforming the resulting products into fluorinated compounds of medicinal interest.
Article
Chemistry, Multidisciplinary
Yun-Cheng Luo, Ming-Kuan Wang, Ling-Chao Yu, Xingang Zhang
Summary: Here, we report a nickel-catalyzed selective C(sp(2))-F bond alkylation of HFO-1234yf with alkylzinc reagents, resulting in 2-trifluoromethylalkenes that can serve as versatile synthons for diversified transformations. Mechanistic studies reveal that the addition of lithium salt is crucial for promoting the oxidative addition of Ni-0(L-n) to the C-F bond, and less electron-rich N-based ligands exhibit comparable or higher oxidative addition rates compared to electron-rich phosphine ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xue-Ying Zhang, Shi-Ping Sun, Yue-Qian Sang, Xiao-Song Xue, Qiao-Qiao Min, Xingang Zhang
Summary: A palladium-catalyzed reductive difluorocarbene transfer reaction that utilizes chlorodifluoromethane as a precursor has been developed, allowing difluorocarbene to couple with two electrophiles. This new mode of difluorocarbene transfer reaction produces difluoromethylated (hetero)arenes from aryl halides/triflates and proton sources, with high functional group tolerance and synthetic convenience. Mechanistic studies reveal an unexpected Pd-0/II catalytic cycle involved in the reductive difluorocarbene transfer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xing Gao, Xiaoxiao Ren, Wei Deng, Xingang Zhang
Summary: This study reports a copper-catalyzed hydrodifluoroallylation of cyclopropenes and alkenyl boronates with 3,3-difluoroallyl sulfonium salts. The reaction shows high efficiency and stereoselectivity, allowing the synthesis of various gem-difluoroallyl cyclopropanes and borylalkanes under mild reaction conditions. The use of chiral phosphine ligand improves the enantioselectivity of the reaction. This method offers synthetic convenience, high functional group tolerance, and synthetic versatility of the resulting products.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenping Ding, Minqi Zhou, Huayu Li, Miao Li, Yanping Qiu, Yu Yin, Lifeng Pan, Wenchao Yang, Yanan Du, Xingang Zhang, Zhijun Tang, Wen Liu
Summary: Modification of organic molecules with fluorine functionalities is a critical approach for developing new pharmaceuticals. In this study, a multienzyme strategy for biocatalytic fluoroalkylation was reported, which involved the use of SAM-dependent methyltransferases and fluorinated SAM cofactors. The strategy demonstrated successful late-stage site-selective fluoroalkylation of the complex molecule vancomycin, with conversions up to 99%.
Article
Chemistry, Physical
Ming-Kuan Wang, Yun-Cheng Luo, Hai-Yang Zhao, Yanxia Zhang, Dawei Zhang, Xingang Zhang
Summary: A cobalt-catalyzed trans-selective arylfluoroalkylation of cyclopentenes has been developed for the efficient synthesis of polysubstituted cyclopentanes. The reaction exhibits broad substrate scope, high functional group tolerance, and synthetic convenience.
Article
Chemistry, Physical
Ling-Chao Yu, Yun-Cheng Luo, Wei Feng, Shu Zhang, Xingang Zhang
Summary: A new organic catholyte material, sodium 2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl-4-yl)-2,2-difluoroacetate (DFTEMPO), is created by introducing a fluorine functionality into 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO), showing higher cell voltage, rate capability, and cycle stability in aqueous redox flow batteries (ARFBs).
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Article
Chemistry, Multidisciplinary
Hao-Wen Li, Yun-Cheng Luo, Ling-Chao Yu, Xingang Zhang
Summary: A palladium-catalyzed gem-difluoroallylation of propargyl sulfonates with gem-difluoroallylboron has been developed, providing a synthetic route to 3,3-difluoro-skipped 1,5-enynes with high efficiency and regioselectivity. The resulting products can serve as versatile synthons for diversified transformations and have potential applications in medicinal chemistry.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Xiaoxiao Ren, Xing Gao, Qiao-Qiao Min, Shu Zhang, Xingang Zhang
Summary: This research reports a novel method for constructing the alkylCF(2)-alkyl bond using alkylzirconocene as a catalyst to promote the reaction between unactivated difluoroalkyl iodides and bromides and alkyl- and silyl-alkenes under visible light irradiation without a catalyst. The resulting difluoroalkylated compounds can serve as versatile synthons in organic synthesis, and the reaction can also be applied to other fluorinated compounds.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
