Article
Chemistry, Applied
Sandor Balazs Kiraly, Laszlo Toth, Tibor Kovacs, Attila Benyei, Erika Lisztes, Balazs Istvan Toth, Tamas Biro, Attila Kiss-Szikszai, Katalin E. E. Kover, Attila Mandi, Tibor Kurtan
Summary: Four series of chiral condensed heterocycles, representing four novel skeletons and exhibiting antiproliferative activity, were synthesized through Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain. The cyclization occurred through four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization, or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a novel route to hydroxyindoles through an inverse Cadogan-type cyclization, where the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and stereoselectivity were studied using DFT calculations, which allowed for proposing a mechanism for the multi-step cyclization to hydroxyindoles and explaining the observed diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Niklas Rauscher, Line Noesborg, Christian Jandl, Thorsten Bach
Summary: In this study, the prezizane-type sesquiterpene agarozizanol B was synthesized through a photochemical cascade reaction, successfully achieving the key step of the synthesis with a specific strategy and obtaining the (+)-enantiomer that is identical to the natural product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Chunxiang Pan, Gaowei Wang, Hengyuan Zhao, Jianxiao Ni, Ruifeng Fan, Yongyun Zhou, Yuanbin Zhu, Shiyuan Wu, Baomin Fan
Summary: An efficient stereoselective cobalt-catalyzed hydrovinylative cyclization of 1,6-enynes with chalcones to obtain functionalized pyrrolidines has been developed. The products were furnished in good yields with up to 93% ee. A plausible mechanism through which the transformation was initiated by cyclization of 1,6-enynes is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Zhe Meng, Jun Yan, Chao Ning, Min Shi, Yin Wei
Summary: This paper presents an efficient synthetic strategy for the rapid construction of multisubstituted pyrroles, furans, and thiophenes via NXS mediated desulfonylative/dehydrogenative cyclization of vinylidenecyclopropanes. The method offers advantages such as a wide substrate range, high efficiency, and synthetic usefulness of the heterocyclic products under metal-free and mild conditions. The derivatization of pyrrole products and the preparation of functional molecules demonstrate the synthetic potential of the products as platform molecules. The reaction mechanism has been investigated through control experiments and DFT calculations.
Review
Chemistry, Multidisciplinary
Ruben Vicente
Summary: This review summarizes key reactivities relying on C-C bond cleavages of cyclopropenes, including both metal-catalyzed and metal-free transformations. The emphasis is on the synthetic utility and mechanistic aspects of various methodologies discussed, covering a range of reactions involving vinyl carbenes, metathesis processes, heterocycles syntheses, SEAr reactions, metalation-ring opening sequences, and cycloadditions. The focus is on results from 2007 to 2019, with relevant pioneering transformations eventually included.
Article
Chemistry, Organic
Biao Guo, Jiaying Lv, Le Lu, Ruimao Hua
Summary: A novel method for constructing the cyclopenta[c]quinoline ring has been developed, which involves the cyclization of 3-bromoindoles with internal alkynes in the presence of palladium. The mechanism of the formation of the cyclopenta[c]quinoline ring is proposed to proceed via a double [1,5] carbonsigmatropic rearrangement of the spirocyclic cyclopentadiene intermediate, generated from the cyclization of 3-bromoindoles with internal alkynes. This study also presents a new ring-expansion reaction of the pyrrole ring to pyridine via one carbon insertion into the C2-C3 bond of indoles, providing a simple and distinct route for constructing tricyclic fused-quinoline derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: This article provides a comprehensive overview of the transformations of yne-allenes, discussing their general and specific reactivities, presenting and commenting on their mechanisms and applications.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Marta Solas, Lorena Renedo, Samuel Suarez-Pantiga, Roberto Sanz
Summary: A gold-catalyzed cascade double cyclization reaction was developed for the synthesis of heterobiaryl compounds, such as furanyl and pyrrolyl 2H-chromenes, from readily available starting materials derived from biomass platform molecules. The reaction involves an initial heterocyclodehydration step followed by an alkyne hydroarylation to form the chromene core.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Veronique Michelet
Summary: The field of gold catalysis has been expanding continuously over the past 20 years, with the discovery of several new rearrangements. Key contributions in this area include the pi-activation of unsaturated substrates and the application of aryl, alkyne, alkene, or keto derivatives.
Article
Chemistry, Organic
Aurelien Galibert-Guijarro, Dominique Mouysset, Liliane Mimoun, Michele P. Bertrand, Laurence Feray
Summary: The one-pot synthesis of 2-aminofurans was achieved through the Mn(OAc)3/Cu(OAc)2-mediated reaction between yna-mides derived from oxazolidone or 3-methylindole carboxylate and cyclic alpha-dicarbonyl radicals. This transformation involves several steps including addition, oxidation, and cyclization, resulting in the formation of persubstituted 2-aminofurans in high yields. This study presents the first radical route for the synthesis of furans from ynamides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Deeksha, Ritesh Singh
Summary: Aza-oxyallyl cations have diverse reactivity profiles for constructing N-scaffolds of biological interest and recent studies have reported new variations in their reactivity, making them versatile tools for organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Anilkumar Gunnam, Alagesan Balasubramani, Goverdhan Mehta
Summary: The recursive anion-mediated activation of o-bis-ynones leads to the one-pot synthesis of 1-indenones, and further reactions result in the access to the embellished cyclopenta[a]inden-8(2H)-one core and its spiroannulated analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Guanghao Huang, Regis Guillot, Cyrille Kouklovsky, Boris Maryasin, Aurelien de la Torre
Summary: A broadly applicable diastereo- and enantioselective inverse-electron-demand Diels-Alder reaction of 2-pyrones and acyclic enol ethers is reported, leading to the synthesis of bridged bicyclic lactones with high yields and enantioselectivities using a copper(II)-BOX catalytic system. Mechanistic studies suggest a stepwise mechanism, and the synthetic potential of the bridged bicyclic lactones is demonstrated through the enantioselective synthesis of polyfunctional cyclohexenes and cyclohexadienes, as well as a carbasugar unit.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Stefano Nejrotti, Cristina Prandi
Summary: This review summarizes the advances in the synthesis and functionalization of furans via gold catalysis between 2016 and 2020, focusing on different synthetic methods, functionalization reactions, and tandem reactions.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Kexin Su, Xin Guo, Liangwei Zhu, Yafeng Liu, Yixuan Lu, Baohua Chen
Summary: A novel radical cross-coupling/cyclization method has been developed for the straightforward synthesis of structurally diverse methylthio-substituted indolizine compounds. In this process, sulfoxonium ylides undergo disproportionation to produce a new type of indolizine derivative, revealing that DMSO does not drop off from sulfoxonium ylides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Juan Feng, Jiayi Shi, Lan Wei, Mingqing Liu, Zhiming Li, Yuanjing Xiao, Junliang Zhang
Summary: In this study, a highly regio- and diastereo-selective palladium/PC-Phos-catalyzed asymmetric Heck/Tsuji-Trost reaction was reported for the synthesis of various functionalized chiral hexahydroindoles with good yields and high enantioselectivity. The application of this reaction to the concise synthesis of (-)-alpha-Lycorane was demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Metallurgy & Metallurgical Engineering
Zhaozhao Yan, Jiongming Zhang, Yanbin Yin, Haitao Ma, Huayang Liu, Xingxing Wu
Summary: This paper studies the influence of embedded steel rod on the current, temperature, and continuous consumption of graphite in the electrode. The results show that with the increase of the radius of the steel rod, the proportion of the current passing through the steel rod increases, and the area of each temperature range above 500 K and the total continuous consumption rate of the electrode decrease.
IRONMAKING & STEELMAKING
(2023)
Review
Chemistry, Multidisciplinary
Yonggui Liu, Yanyan Wang, Xingxing Wu, Yonggui Robin Chi
Summary: In this personal account, the recent work on exploring new activation modes of NHC catalysis towards molecular complexity is summarized, focusing on the development and applications of NHC to achieve diversity and enantioselectivity in the preparation of functional molecules.
Article
Chemistry, Multidisciplinary
Meng Wu, Jian-Bin Zhang, Yi-Wei Xiong, Yong-Xu Zhao, Meng-Ge Zheng, Xia-Li Huang, Fang Huang, Xing-Xing Wu, Xue Li, Wei-Jiao Fan, Lin Hu, Yuan-Yuan Zeng, Xia-Ju Cheng, Ji-Cheng Yue, Juan-Juan Du, Nan-Nan Chen, Wen-Xiang Wei, Qing-Hua Yao, Xiao-mei Lu, Chao Huang, Jiong Deng, Zhi-Jie Chang, He-Bin Liu, Ting C. Zhao, Y. Eugene Chinn
Summary: By regulating the acetylation of extracellular proteins, eSIRT2 can promote cancer cell metastasis, and the deacetylation mechanism of eSIRT2 in tumor microenvironment has been revealed.
Article
Chemistry, Multidisciplinary
Chun Ma, Yue Sun, Junfeng Yang, Hao Guo, Junliang Zhang
Summary: In this study, an efficient method for the catalytic synthesis of Troger's base analogues with nitrogen stereocenters was reported. The process involved palladium catalysis and the use of home-developed GF-Phos. The method allowed for the rapid construction of a new rigid cleft-like structure with both C and N stereogenic centers, exhibiting excellent efficiency and selectivity. Various applications as a chiral organocatalyst and metallic catalyst precursors were demonstrated, and DFT calculations revealed that NH center dot center dot center dot O hydrogen bonding and weak interaction between the substrate and ligand played crucial roles in achieving excellent enantioselectivity control.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Fen Su, Juan Zou, Xiaokang Lv, Fengfei Lu, Yijie Long, Kun Tang, Benpeng Li, Huifang Chai, Xingxing Wu, Yonggui Robin Chi
Summary: The development of catalyst-controlled methods for direct functionalization of two distinct C-H bonds is an appealing approach for C-C formations in synthetic chemistry. This article describes an organocatalytic approach using readily available aldehyde as acyl source, which allows for the straightforward acylation of C(sp(3))-H bonds involving dehydrogenative coupling of aldehydes with ether, amine, or benzylic C(sp(3))-H bonds. The developed method provides a wide range of ketones under mild conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Youshao Tu, Bing Xu, Qian Wang, Honglin Dong, Zhan-Ming Zhang, Junliang Zhang
Summary: In this work, we developed a highly enantioselective Pd/TY-Phos-catalyzed Heck/Tsuji-Trost reaction of o-bromophenols with various 1,3-dienes, allowing expedient access to chiral substituted 2,3-dihydrobenzofurans. This reaction features excellent regio-and enantiocontrol, high functional group tolerance, and easy scalability. More importantly, the demonstration of this method as a highly valuable tool for the construction of optically pure natural products (R)-tremetone and fomannoxin is highlighted.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Shiquan Gao, Chen Wang, Junfeng Yang, Junliang Zhang
Summary: In this study, an enantioselective intramolecular reductive coupling of enynes was achieved via the combination of electrochemistry and cobalt catalysis. The transition-metal catalyzed asymmetric cyclization of 1,6-enynes has been widely used for the construction of carbocycles and heterocycles, but examples under electrochemical conditions are rare. We report a Co-catalyzed enantioselective intramolecular reductive coupling of enynes using H2O as the hydride source, which provides good yields with high regio- and enantioselectivities. This study represents a rare progress on the cobalt-catalyzed enantioselective transformation via electrochemistry with a general substrate scope, and DFT studies suggest the possible reaction pathways.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Li-Ming Zhang, Wenjun Luo, Jiangzhen Fu, Yu Liu, Junliang Zhang
Summary: A newly developed PNP-type W-Phos ligand showed a unique effect on the catalytic asymmetric addition of reactive Grignard reagents to ketimines. This enabled a Cu(I)-catalyzed asymmetric alkylation reaction of N-sulfonyl ketimines, resulting in the formation of optically active α-tertiary amines with high enantioselectivities.
Article
Chemistry, Medicinal
Qi Wu, Xingxing Wu, Mao Wang, Kexin Liu, Yuge Li, Xiaoyu Ruan, Lin Qian, Lingchang Meng, Zhiting Sun, Lei Zhu, Jing Wu, Genglin Mu
Summary: Using network pharmacology, baicalin's targets and pathways were predicted for its potential benefit in treating inflammatory bowel disease. Experimental colitis was induced and metabolomics was used to identify differential metabolites and associated metabolic pathways. Network pharmacology and integrated analysis of metabolomics revealed the primary targets and key metabolites of baicalin against experimental colitis.
DRUG DESIGN DEVELOPMENT AND THERAPY
(2023)
Article
Hospitality, Leisure, Sport & Tourism
Xingxing Wu, Logan Schuetz, Milae Lee, Laura L. Payne, Kimberly J. Shinew
Summary: The purpose of this study was to investigate the motivations and meanings of being a NDWB season ticket holder among older women. The findings indicated that being season ticket holders fostered a strong sense of identification with the team and allowed the older women to enhance their social contacts and friendships with other women, fostering a sense of community.
JOURNAL OF LEISURE RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Fen Su, Fengfei Lu, Kun Tang, Xiaokang Lv, Zhongfu Luo, Fengrui Che, Hongyan Long, Xingxing Wu, Yonggui Robin Chi
Summary: This study discloses the first organocatalytic direct functionalization/acylation of inert C(sp3)-H bonds of completely unfunctionalized alkanes. The approach involves N-heterocyclic carbene catalyst-mediated carbonyl radical intermediate generation and coupling with simple alkanes through the corresponding alkyl radical intermediates generated via a hydrogen atom transfer process. This method provides a new avenue for functionalization of challenging C-H bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Yanyan Wang, Yonggui Liu, Sha Zhao, Yijie Long, Xingxing Wu
Summary: The development of catalyst-controlled synthetic strategies for enantioselective access to carbon-heteroatom bonds has attracted significant interest in the field of organic chemistry. N-heterocyclic carbene (NHC) organocatalysis has been extensively explored in the past few decades to rapidly assemble asymmetric carbon-heteroatom bonds in novel chemical transformations. Various activation modes and NHC-derived intermediates, such as Breslow intermediates and acyl azoliums, have shown substantial potential in constructing carbon-heteroatom bonds. This review summarizes recent advances in stereoselective carbon-heteroatom bond forming reactions enabled by NHC organocatalysis, with a focus on new activation modes and reactive intermediates, aiming to inspire unique insights into the preparation of chiral functional molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Multidisciplinary
Bing Xu, Quanpu Wang, Chao Fang, Zhan-Ming Zhang, Junliang Zhang
Summary: This review summarizes the latest advancements in enantioselective palladium-catalyzed cyclization reactions over the past eleven years. The review is organized into thirteen sections based on the different types of transformations involved. Chiral palladium catalysts have shown outstanding features in promoting a plethora of enantioselective cyclization reactions, providing convenient access to structurally diverse chiral carbo- and hetero-cycles.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Zhi-Mao Zhang, Junliang Zhang, Quan Cai
Summary: In this study, seven pentacyclic 19-nor-clerodane diterpenoids were collectively synthesized using an asymmetric reaction. A key feature of the synthesis was the generation of a versatile intermediate through late-stage oxidation state adjustments. This study provides a concise and efficient synthetic route for these compounds.
