Article
Chemistry, Multidisciplinary
Won Jun Jang, Jeongkyu Woo, Jaesook Yun
Summary: The study reported a method to synthesize enantioenriched alkylboron compounds through conjugate addition, which are influenced by two contiguous carbon stereogenic centers, with high yield and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Chandan K. Mahato, Sayan Mukherjee, Mrinalkanti Kundu, Virbhadra P. Vallapure, Animesh Pramanik
Summary: This study utilized a new set of organic catalysts for asymmetric Michael reactions in water, achieving high efficiency and yield, offering a new method for green synthesis. The strategy also successfully synthesized an optically active octahydroindole, a key component found in many natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Ziyin Kong, Weipeng Hu, James P. P. Morken
Summary: A Pt-catalyzed hydrosilylation reaction of (Z)-1,2-diborylethylene leads to the formation of a 1,2-diboryl-1-silylalkane, which can be used in catalytic cross-coupling reactions. Depending on the catalyst and the reaction conditions, the coupling can occur at either the α or β position relative to the silane center.
Article
Chemistry, Organic
Xiangjie Chen, Yi An, Guangfen Du, Yujie Zhao, Lin He, Jixing Zhao, Shi-Wu Li
Summary: This study established a method for asymmetric catalytic vinylogous Michael addition of 2-methyl-3,5-dinitrobenzoates to unsaturated ketones using chiral rhodium catalysts. This strategy successfully synthesized a variety of optically pure compounds containing imidazole and 3,5-dinitrobenzene skeletons.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chenghao Li, Wei-Fang Zuo, Jin Zhou, Wu-Jingyun Zhou, Meng Wang, Xiang Li, Gu Zhan, Wei Huang
Summary: In this study, axially chiral 3,4'-indole-pyrazole derivatives were successfully synthesized through the chiral phosphoric acid-catalyzed Mannich reaction. High diastereoselectivities and enantioselectivities could be obtained in most cases. The presence of a 5-pyrazolyl acetate moiety in the substrate proved crucial for improving the reactivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Huimyoung Byeon, Sunghyeon Ryu, Eun Jeong Yoo, Jung Woon Yang
Summary: Substrate-controlled cascade reactions between alpha,beta-unsaturated aldehydes or their analogues and 2,4-dinitrobenzyl chloride in the presence of a chiral secondary amine catalyst and base lead to a variety of alpha-benzylated enals and enantioenriched cyclopropane-fused chroman-2-one derivatives. The cyclopropane-tethered iminium ion plays a key role in these reactions to determine stereochemical outcomes, supported by a control experiment.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Hang-Fei Tu, Alienor Jeandin, Marcos G. Suero
Summary: In this study, a catalytic one-step synthesis of cyclopropenium cations using readily available alkynes and hypervalent iodine reagents as carbyne sources is reported. A novel Rh-carbynoid catalytically generates monovalent cationic carbynes (:C+-R), which are then transferred to alkynes via an oxidative [2+1] cycloaddition, resulting in a new type of ester-substituted CPC. This method allows for regioselective attack of various carbon and heteroatomic nucleophiles, providing a new platform for the synthesis of valuable cyclopropenes that are difficult or impossible to make by current methodologies.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Zhi-Xin Zhang, Li-Gao Liu, Yi-Xi Liu, Jian Lin, Xin Lu, Long-Wu Ye, Bo Zhou
Summary: Catalytic enantioselective transformation of alkynes is an important method for synthesizing axially chiral molecules. This study presents an organocatalytic approach for the atroposelective intramolecular (4 + 2) annulation of enals with ynamides. The method allows for the efficient and atom-economical preparation of various axially chiral 7-aryl indolines with good enantioselectivity. Computational studies were conducted to understand the regioselectivity and enantioselectivity, and a chiral phosphine ligand derived from the synthesized molecules showed potential for asymmetric catalysis.
Article
Chemistry, Organic
Xiaoxiao Song, Yanjun Fan, Zhiming Zhu, Qijian Ni
Summary: We have developed a highly straightforward strategy for the synthesis of a new axially chiral 3-arylindolizine scaffold using chiral phosphoric acid catalyst. The reaction showed good scalability and yielded a series of axially chiral 3-arylindolizines with excellent enantioselectivity. This approach not only has a broad substrate scope and mild reaction conditions, but also demonstrates the potential utility of the formed axially chiral compounds.
Review
Chemistry, Multidisciplinary
Ming Xiang, Dana E. Pfaffinger, Michael J. Krische
Summary: This review exhaustively catalogs the use of allenes and 1,3-dienes as chiral allylmetal pronucleophiles in intermolecular catalytic enantioselective reductive additions, along with redox-neutral hydrogen auto-transfer processes. The review highlights the ability of these compounds to serve as tractable non-metallic pronucleophiles, leading to many novel transformations that are not possible with traditional allylmetal chemistry.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Deyun Qian, Srikrishna Bera, Xile Hu
Summary: A nickel-catalyzed hydroalkylation method has been developed to assemble a wide range of chiral alkyl amines with high regio- and enantioselectivity from enecarbamates and alkyl halides. The method is suitable for both nonactivated and activated alkyl halides, producing enantiomerically enriched amines with high functional group tolerance.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Osamu Kitagawa
Summary: Biaryl atropisomers, as key structural components in various compounds, have been recently studied for their catalytic asymmetric syntheses and applications in asymmetric reactions. Previously overlooked, these compounds have now become a popular research area in synthetic organic chemistry, with successful applications in various synthetic reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Chemistry, Multidisciplinary
Fei Ye, Zheng Xu, Li-Wen Xu
Summary: The development of highly effective chiral ligands is crucial for enhancing catalytic activity and selectivity in metal-catalyzed asymmetric synthesis. Our group has designed and synthesized a series of new chiral catalysts based on the concept of nonequivalent coordination to access products with excellent chemo-, diastereo-, and enantioselectivity. These ligands have demonstrated good to excellent performance in constructing quaternary carbon/silicon and multiple stereogenic centers with enantioselectivity.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Yimin Hu, Wangyu Shi, Zhengyang Yan, Jianning Liao, Min Liu, Jiaqing Xu, Wei Wang, Yongjun Wu, Cheng Zhang, Hongchao Guo
Summary: An efficient method using K2CO3 catalysis has been developed for the 1,4-addition/intramolecular cyclization/aromatization reaction of aurone-derived 1-azadienes with trisubstituted allenoates, resulting in a series of benzofuro[3,2-b]pyridines in moderate to excellent yields. The reaction proceeds efficiently under an air atmosphere without the need for transition metal catalysts, providing a concise approach to benzofuro[3,2-b]pyridines.
Article
Chemistry, Organic
Christian Wulkesch, Constantin Czekelius
Summary: The study highlights a mild, operationally simple, and inexpensive photocatalytic perfluoroalkenylation reaction for the direct synthesis of tetrasubstituted, highly electron-deficient enals from aldehydes. The one-step reaction is tolerant to various functional groups and can be applied to a wide range of substrates, with product yields ranging from 52-84%.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Agriculture, Multidisciplinary
Huimin Zhao, Aiping Yang, Nan Zhang, Shiyang Li, Tianjie Yuan, Ning Ding, Siwang Zhang, Sheng Bao, Chang Wang, Yinan Zhang, Xiachang Wang, Lihong Hu
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Zheng Cui, Jonathan Overbay, Xiachang Wang, Xiaodong Liu, Yinan Zhang, Minakshi Bhardwaj, Anke Lemke, Daniel Wiegmann, Giuliana Niro, Jon S. Thorson, Christian Ducho, Steven G. Van Lanen
NATURE CHEMICAL BIOLOGY
(2020)
Article
Chemistry, Medicinal
Yang Liu, Joseph M. Eckenrode, Yinan Zhang, Jianjun Zhang, Reiya C. Hayden, Annet Kyomuhangi, Larissa Ponomareva, Zheng Cui, Jurgen Rohr, Oleg Tsodikov, Steven G. Van Lanen, Khaled A. Shaaban, Markos Leggas, Jon S. Thorson
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Organic
Jing Jiang, Dandan Yuan, Congzhe Ma, Wanbin Song, Yaoyu Lin, Lihong Hu, Yinan Zhang
Summary: An efficient divergent approach of Pd-catalyzed C-H oxygenation of polyaromatic rings is described, utilizing reversible directing groups to achieve regiospecific oxygenation. Mechanistic investigation, including deuterium-labeling experiments and DFT calculations, reveals the crucial role of tunable ligand-assisted C-H bond cleavage during the reaction process.
Article
Pharmacology & Pharmacy
Qi Lv, Yao Xing, Jian Liu, Dong Dong, Yue Liu, Hongzhi Qiao, Yinan Zhang, Lihong Hu
Summary: The study reveals that lonicerin exerts therapeutic effects on intestinal inflammation by modifying autophagy through EZH2-mediated pathways. The EZH2/ATG5/NLRP3 axis may serve as a novel strategy to prevent ulcerative colitis and other inflammatory diseases.
ACTA PHARMACEUTICA SINICA B
(2021)
Article
Immunology
Qi Lv, Yao Xing, Dong Dong, Yang Hu, Qingzhu Chen, Linhui Zhai, Lihong Hu, Yinan Zhang
Summary: Costunolide, a main active component of Radix Aucklandiae, demonstrated significant anti-inflammatory and immunomodulation effects in the study, by rebalancing Th17/Treg cells and reducing the levels of proinflammatory cytokines. The mechanism involved the inhibition of HIF-1 alpha-mediated glycolysis specifically in Th17 cells, which could potentially provide a new perspective on immune-metabolism therapy for colitis.
INTERNATIONAL IMMUNOPHARMACOLOGY
(2021)
Article
Plant Sciences
Li Rao, Yao Li, Qian He, Yu Liu, Yu Su, Yun-Xia You, Yue Fan, Bin Lin, Yi-Nan Zhang, Chuan-Rui Zhang
Summary: In this study, eleven new iridoids, brachybones A-K (1-11), were isolated from the twigs of Viburnum brachybotryum. The structures of the compounds were determined through spectroscopic data analysis and electronic circular dichroism (ECD) spectra. Compounds 10 and 11 were found to exhibit cytotoxic activity against HCT-116 cells.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Organic
Weichen Dai, Jie Zheng, Xinyu Yan, Wei Tang, Lihong Hu, Yinan Zhang
Summary: This study describes the synthesis of (±)-epi-Costunolide from (E,E)-farnesol through a seven-step procedure, with the key step being an intramolecular allylation using a chromium(II)-mediated Nozaki-Hiyama-Kishi reaction. It was found that epi-Costunolide is a moderate inhibitor of B lymphocyte proliferation based on anti-inflammatory screening results.
Article
Biochemistry & Molecular Biology
Jonathan A. Clinger, Yinan Zhang, Yang Liu, Mitchell D. Miller, Ronnie E. Hall, Steven G. Van Lanen, George N. Phillips, Jon S. Thorson, Sherif Elshahawi
Summary: This study identified the ter gene cluster in the Appalachian Streptomyces strain RM-S-8 responsible for producing terfestatins B and C, as well as echoside B. It characterizes the dual enzyme system of TerB/C, with TerB acting as a reductase and TerC as a dehydratase in the biosynthesis of natural terphenyls. X-ray crystallography of both enzymes provides mechanistic insights, while mutagenesis validation of the TerC structural model highlights the critical role of arginine 143 and aspartate 173 in catalysis. Overall, this work advances our understanding of early steps in terphenyl biosynthesis.
ACS CHEMICAL BIOLOGY
(2021)
Article
Chemistry, Medicinal
Qi Lv, Xiang Pan, Dan Wang, Quanjin Rong, Ben Ma, Xiaolong Xie, Yinan Zhang, Junwei Wang, Lihong Hu
Summary: Inhibiting tumor-associated macrophages by blocking CSF-1/CSF-1R signal has become a promising strategy for cancer immunotherapy. A novel series of orally highly effective CSF-1R inhibitors were designed, among which compound 21 showed excellent inhibitory activity and potent antiproliferative effects against colorectal cancer cells. Additionally, compound 21 demonstrated superior efficacy over PLX3397 in vivo, making it a promising candidate for colorectal cancer immunotherapy.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yujian Mao, Jing Jiang, Dandan Yuan, Xiuzhen Chen, Yanan Wang, Lihong Hu, Yinan Zhang
Summary: Methyl groups are commonly found in bioactive molecules, and site-specific methylation has become an important strategy for their structural functionalization. In this study, a highly regioselective peri- and ortho-C-H methylation of 1-naphthaldehyde was achieved using a transient ligand strategy, leading to the synthesis of various methyl-substituted naphthalene frameworks. The mechanism of peri-methylation and ortho-methylation was investigated, providing insights into the control factors and energetically favorable pathways.
Article
Plant Sciences
Qian He, Simin Li, Yue Fan, Yu Liu, Yu Su, Zhen Zhou, Yi-Nan Zhang, Guo-Li Li, Li Rao, Chuan-Rui Zhang
Summary: Nine new complex flavanones, named cryptometcones A-I (1-9), along with four known analogues, were isolated from Cryptocarya metcalfiana. Their structures and absolute configurations were determined through spectroscopic data analysis and ECD calculations. Compounds 3-5, 8, and 9 exhibited cytotoxicity against the HCT-116 cancer cell line.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Organic
Yujian Mao, Zhen Xia, Lihong Hu, Yinan Zhang
Summary: In this study, new methods for synthesizing methylated naphthalene natural products were disclosed using simple and commercially available naphthalene molecules. These methods overcome the challenges of low content in plants and lack of synthetic methods.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Ping Wang, Hongqiong Yang, Weijiang Lin, Jingxian Zhou, Chengli Yu, Yinan Zhang, Yi Liu, Lingyu Ma, Mengting Li, Yang Hu, Qi Lv, Jian Liu, Lihong Hu
Summary: The D5 compound has been found to inhibit the differentiation of Th17 cells by suppressing PKM2-mediated glycolysis, restoring the Th17/Treg balance, and showing promising therapeutic effects against ulcerative colitis, making it a potential novel anti-UC candidate.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Jing Jiang, Yujian Mao, Yaoyu Lin, Jiayi Shen, Yinan Zhang
Summary: This article presents a total synthesis of hemigossypol through ligand-directed C-H oxygenations and completing the synthesis in 10 steps with a total yield of 9.5%. By adjusting the order of hydroxyl and isopropyl group installation, our strategy based on direct functionalization of a naphthalene ring shortens the route and improves efficiency compared to conventional approaches. This regiospecific approach holds promise for rapid access to diverse derivatives of gossypol for biological studies.
ORGANIC CHEMISTRY FRONTIERS
(2023)
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)
