Article
Chemistry, Multidisciplinary
Fabian Severin, Giovanni M. Fusi, Christina Wartmann, Jorg-Martin Neudoerfl, Albrecht Berkessel
Summary: In this study, we report a highly syn-selective epoxidation method for terminal allylic alcohols using a titanium salalen complex catalyst at room temperature and aqueous hydrogen peroxide as oxidant. The results demonstrate that enantiopure terminal allylic alcohols can be efficiently converted to epoxy alcohols with high yields and excellent syn-diastereoselectivity. This method shows great synthetic potential and is demonstrated by the gram-scale preparation of a tetrahydrofuran building block with three stereocenters.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jianguo Yang, Saimei Liu, Jing Gui, Daokai Xiong, Jinshan Li, Zhiming Wang, Jun Ren
Summary: A highly selective hydroxyalkylation of aniline derivatives with arylglyoxal hydrates has been achieved using HFIP as a catalyst. The reaction provides efficient synthesis of various N,N-dialkylanilines and their derivatives with alpha-hydroxy carbonyl units under mild conditions. The method has shown great synthetic potential by enabling the facile synthesis of several structurally interesting molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Youka Bunno, Yuta Tsukimawashi, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Summary: Metal-containing Schiff base/sulfoxides were developed as chiral ligands for Pd(II)-catalyzed asymmetric intramolecular allylic C-H amination reactions, showing good performance in tuning the selectivity and reactivity of the Pd(II)-catalyst with high product yields.
Article
Chemistry, Multidisciplinary
Kristen E. Berger, Raymond J. Martinez, Jianhan Zhou, Christopher Uyeda
Summary: Gem-dichloroalkanes can be used as precursors for asymmetric cyclopropanation reactions of alkenes. The process involves a cobalt catalyst and shows high levels of enantioselectivity for monosubstituted, 1,1-disubstituted, and internal alkenes. The reaction is compatible with alkyl-substituted carbenes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Aleksey Zerov, Irina A. Boyarskaya, Olesya Khoroshilova, Irina N. Lavrentieva, Alexander Slita, Ekaterina O. Sinegubova, Vladimir V. Zarubaev, Aleksander V. Vasilyev
Summary: Trimethylsilyl ethers of 1,5-diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-oles in the superacid TfOH give rise to reactive conjugated CF3-allylic-propargylic cations, which, in the presence of arenes and excess TfOH, lead to the formation of E-1,1,5-triaryl-3-(trifluoromethyl)-pent-2-en-4-ynes and CF3-bicyclic dihydroanthracene derivatives, respectively. These two main reaction pathways are dependent on the nucleophilicity of aryl substituents in CF3-pentenynes and external aromatic molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Marzena Wosinska-Hrydczuk, Jacek Skarzewski
Summary: The paper describes the synthesis of new chiral ligands, including chiral pyridine-containing beta-amino alcohols synthesized by opening epoxides with enantiomeric 1-phenylethylamine, and their conversion into new complexing pyridine-containing seleno- and thioethers. The diastereoselective reaction outcomes were discussed based on DFT optimized structures of diastereomeric sulfonamidates. New amino-aldimine ligands were also synthesized and tested in Tsuji-Trost allylic alkylation, with stereochemical induction agreeing with nucleophilic attack at the allylic carbon opposite to complexing nitrogen of pyridine.
Review
Chemistry, Physical
Xue-Xin Zhang, Ying Zhang, Ling Liao, Yang Gao, Heng E. M. Su, Jin-Sheng Yu
Summary: This minireview summarizes the recent advancements in catalytic enantioselective isomerization and tandem reactions, discusses their advantages and limitations, and highlights the synthetic opportunities for further development.
Article
Chemistry, Multidisciplinary
Martin S. Maier, Andrej Shemet, Dirk Trauner
Summary: The 2'-phosphodiesterase inhibitor A-74528 is a complex type II polyketide with intriguing biosynthesis and unusual biological activity. This study focuses on the synthesis of A-74528, specifically the construction of its carbon skeleton and the installation of its stereocenters. The strategy involves various reactions to establish carbocycles and append the pyrone moiety.
Review
Chemistry, Inorganic & Nuclear
Manoj Kumar, Atresh Kumar Singh, Alok Kumar Singh, Rajesh K. Yadav, Satyam Singh, Atul P. Singh, Amit Chauhan
Summary: Schiff bases have been widely studied in coordination chemistry for their reactivity and adaptable metal complexes. They have numerous applications in various fields, including catalysis, material science, and bioinorganic chemistry. This review focuses on Schiff bases derived from salicylaldehyde and their derivatives, with a specific emphasis on their synthesis, characterization, and applications in metal complexes. The article provides important knowledge for researchers in this field and encourages further research in Schiff base complexes.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Organic
Masahiro Sai
Summary: The isomerization of allylic alcohols is an important reaction, and this paper reports the development of an efficient catalytic system that allows for the isomerization of a broad range of substrates with high yields. The catalytic system was also successfully applied to a tandem reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yang Liu, Linghong Zhang, Yong Zhang, Shanshan Cao, Xu Ban, Yanli Yin, Xiaowei Zhao, Zhiyong Jiang
Summary: In this article, a photoredox catalytic hydrogen atom transfer (HAT) and enantioselective protonation strategy for asymmetric olefin isomerization is reported. A dual catalyst system involving a visible light photosensitizer DPZ and a chiral phosphoric acid is established, with the assistance of N-hydroxyimide to perform HAT. This strategy enables the synthesis of a wide array of allylic azaarene derivatives with high yields, ees, and E/Z ratios, highlighting its broad applicability and promising utility.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Masahiro Sai
Summary: This study introduces a novel base-promoted reaction method for the diastereoselective synthesis of 1,3-diols with three contiguous stereogenic centers from allylic alcohols and aldehydes via allylic isomerization-initiated Aldol-Tishchenko reactions. Unlike traditional systems, this method utilizes readily available allylic alcohols as nucleophiles instead of enolizable aldehydes and ketones, offering a more sustainable and efficient approach to complex diol synthesis.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Review
Chemistry, Inorganic & Nuclear
David Izuchukwu Ugwu, Jeanet Conradie
Summary: This review focuses on the synthesis and applications of metal complexes containing bidentate ligands, which have shown various medicinal properties such as anticancer, antiproliferative, antimalarial, anti-inflammatory, antioxidant, and antifungal activities. These metal complexes exhibit selective complexation with central metal atoms to inhibit the activities of metalloenzymes. They have also been identified as versatile catalysts in organic synthesis. Remarkably, some of these complexes have demonstrated better efficacy compared to existing commercial therapeutic agents.
INORGANICA CHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Jian Shen, Zhongyun Xu, Shuo Yang, Shengxiao Li, Jie Jiang, Yong-Qiang Zhang
Summary: The development of catalytic and enantioselective allylation of epoxides, which can deliver a range of quaternary stereocenters, is a significant challenge in organic synthesis. In this study, the researchers demonstrate the first highly regio- and enantioselective allylation of epoxides using earth-abundant titanium and a sophisticated salen ligand. The resulting allylation products are multifunctional building blocks that can be further elaborated to stereodefined compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Yujie Wang, Shihan Liu, Haobo Yang, Hengxu Li, Yu Lan, Qiang Liu
Summary: Research shows that a higher efficiency can be achieved by substituting an N-M' group (M' = alkali metals) for the N-H moiety using a large excess of metal alkoxides (M'OR), but the metal-hydride amidate intermediate has not yet been isolated. Furthermore, it is found that M/NM' bifunctional catalysis is superior to classic M/NH bifunctional catalysis in hydrogenation reactions.
Article
Chemistry, Multidisciplinary
Yu-Li Sun, Xing-Ben Wang, Feng-Na Sun, Qian-Qian Chen, Jian Cao, Zheng Xu, Li-Wen Xu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Physical
Qing Wang, Fei Ye, Jian Cao, Zheng Xu, Zhan-Jiang Zheng, Li-Wen Xu
CATALYSIS COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Jun-Han Ma, Li Li, Yu-Li Sun, Zheng Xu, Xing-Feng Bai, Ke-Fang Yang, Jian Cao, Yu-Ming Cui, Guan-Wu Yin, Li-Wen Xu
SCIENCE CHINA-CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Zhao Li, Xu Wang, Yu-Ming Cui, Jun-Han Ma, Li-Lei Fang, Lu-Lu Han, Qin Yang, Zheng Xu, Li-Wen Xu
Summary: The study successfully combined palladium-catalyzed DKR with C-H functionalization to synthesize non-biaryl-atropisomer-type (NBA) axially chiral organosilanes, providing a new approach for the synthesis of multifunctional axially chiral organosilicon compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Xiao-Bing Chen, Li Li, Wan-Chun Yang, Kun-Long Song, Bin Wu, Wan-Er Gan, Jian Cao, Li-Wen Xu
Summary: In this study, a novel palladium-catalyzed C-C bond activation of methylenecyclobutanes followed by Suzuki cross-coupling reaction was reported, leading to the formation of multisubstituted indanes. The tandem reaction process involves intramolecular carbopalladation of double bond, beta-carbon elimination, and intermolecular trapping of the transient sigma-alkylpalladium complex with boronic acids. A new TADDOL-derived phosphoramidite ligand containing fluorine and silicon-based bulky groups was found to be efficient for C-C bond activation of methylenecyclobutanes.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Wan-Chun Yang, Xiao-Bing Chen, Kun-Long Song, Bin Wu, Wan-Er Gan, Zhan-Jiang Zheng, Jian Cao, Li-Wen Xu
Summary: This study demonstrated a palladium-catalyzed asymmetric tandem C-C bond activation/Cacchi reaction between cyclobutanones and o-ethynylanilines, leading to the synthesis of one-carbon-tethered chiral indanone-substituted indoles with multiple new bonds and stereocenters.
Article
Chemistry, Multidisciplinary
Jia-Le Xie, Zheng Xu, Han-Qi Zhou, Yi-Xue Nie, Jian Cao, Guan-Wu Yin, Jean-Philippe Bouillon, Li-Wen Xu
Summary: The study presents a highly enantioselective hydrosilylation of ynones using a palladium catalyst with a chiral ligand, leading to the formation of a series of silicon-stereogenic silylenones with high yield and enantioselectivity. The reaction mechanism and origin of high degree of stereoselectivity were elucidated through density functional theory calculations, highlighting the importance of aromatic interactions in the reaction.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Organic
Fei Ye, Li-Wen Xu
Summary: Silicon and its related organosilicon chemistry have become integral parts of synthetic chemistry due to their ability to participate in various organic transformations. The advances in catalytic hydrosilylation and synthesis of silicon-stereogenic silanes demonstrate the significance and potential of organosilicon chemistry in academic research and industrial applications.
Article
Chemistry, Multidisciplinary
Hui-Lin Li, Wei-Sheng Huang, Fang-Ying Ling, Li Li, Jun-Hao Yan, Hao Xu, Li-Wen Xu
Summary: Organosilicon compounds are important reagents and intermediates in the construction of new materials and complex products. In this study, a highly diastereoselective rhodium-catalyzed cycloisomerization reaction was demonstrated using (EtO)3SiH to accelerate the cyclization reaction and yield spiro-fused succinimide and pyrazolone derivatives as a single diastereoisomer. The proposed mechanism involves an active Rh-H species from the hydrosilane as the H-donor in the spiro-type cycloisomerization reaction.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Kun-Long Song, Bin Wu, Wan-Er Gan, Wan-Chun Yang, Xiao-Bing Chen, Jian Cao, Li-Wen Xu
Summary: The palladium-catalyzed carbonylative C-C bond activation reaction described in this study involves C-C bond cleavage, ring-opening, and amino- or alkoxycarbonylation reactions on cyclobutanones. Two C-C bonds and one C-O or C-N bond are formed under gas-free conditions using CO surrogates, yielding a variety of indanones with ester or amide groups.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Qiu-Qi Mu, Yi-Xue Nie, Hang Li, Xing-Feng Bai, Xue-Wei Liu, Zheng Xu, Li-Wen Xu
Summary: This study achieved highly enantioselective kinetic resolution of sterically hindered benzylamines for the first time through transition-metal-catalyzed oxidative carbonylation, providing a new approach to chiral isoindolinones (er up to 97:3). The origin of chemoselectivity and stereoselectivity was confirmed by density functional theory (DFT) calculations.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Li Li, Yun-Long Wei, Li-Wen Xu
Article
Chemistry, Multidisciplinary
Qiu-Chao Mu, Yi-Xue Nie, Xing-Feng Bai, Jing Chen, Lei Yang, Zheng Xu, Li Li, Chun-Gu Xia, Li-Wen Xu
Article
Chemistry, Multidisciplinary
Feng-Na Sun, Wan-Chun Yang, Xiao-Bing Chen, Yu-Li Sun, Jian Cao, Zheng Xu, Li-Wen Xu
Article
Chemistry, Multidisciplinary
Qiao-Ying Sun, Zhao Li, Zheng Xu, Zhan-Jiang Zheng, Jian Cao, Ke-Fang Yang, Yu-Ming Cui, Li-Wen Xu
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
