Article
Chemistry, Organic
Mohammed Anif Pasha, K. Anebouselvy, Dhevalapally B. Ramachary
Summary: Lawsone, a red-orange dye found in henna leaves, is an important building block in the fields of chemistry and biology. In recent decades, the chemistry of lawsone has gained significant interest among synthetic organic chemists. This review summarizes the latest advances in the asymmetric synthesis of high-yielding, optically active molecules using lawsone and lawsone derivatives as key building blocks.
Review
Chemistry, Applied
Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi
Summary: Pyrazoleamides have gained attention as reactive and practical surrogates in asymmetric catalysis, particularly in a variety of metal- and organocatalytic transformations. Their relevance has extended to photoredox catalysis and challenging stereoselective bond-forming reactions in recent years.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Vojtech Docekal, Tereza Koberova, Jan Hrabovsky, Andrea Vopalenska, Robert Gyepes, Ivana Cisarova, Ramon Rios, Jan Vesely
Summary: A new asymmetric organocatalytic cascade reaction was reported for the synthesis of enantiopure chiral boron dipyrromethenes (BODIPYs), with high isolated yields and enantiomeric excesses. The method showed synthetic versatility and was successfully applied to a series of additional transformations of the corresponding optically pure compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Wei Liu, Tianren Qin, Wansen Xie, Jinmiao Zhou, Zidan Ye, Xiaoyu Yang
Summary: We have developed an efficient modular asymmetric synthesis of azahelicenes from readily available polycyclic aromatic amines, aldehydes, and (di)enamides, employing a central-to-helical chirality conversion strategy. A series of aza[5]- and aza[4]helicenes bearing various substituents were easily obtained with good yields and high enantioselectivities. The diverse derivatizations and the preliminary application of the azahelicene derivative as a chiral organocatalyst demonstrated the potential of this method, and the photophysical and chiroptical properties of these azahelicenes were well studied, showing potential applications in novel organic optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Helene Pellissier
Summary: This review discusses the major advancements in the total synthesis of bioactive products using enantioselective organocatalytic domino/tandem reactions as key steps, including those based on asymmetric Michael-initiated domino reactions and aldol-initiated domino/tandem reactions.
CURRENT ORGANIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Leon Hoppmann, Olga Garcia Mancheno
Summary: The review focuses on the organocatalytic applications of silyl-dienolates in asymmetric vinylogous C-C bond formations, highlighting their high regioselectivities and catalytic characteristics.
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.
Review
Chemistry, Applied
Helene Pellissier
Summary: This review provides an update on the field of enantioselective domino reactions catalyzed by chiral catalysts derived from noble metals, such as palladium, silver, rhodium, ruthenium, iridium, and gold, since the beginning of 2019. It showcases the diverse range of these catalysts, enabling unprecedented asymmetric domino reactions with excellent enantioselectivity and providing access to a wide variety of complex chiral molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Muhammad Sohail, Fujie Tanaka
Summary: The DYKAT reactions can transform dihydrobenzofuranone derivatives into spirooxindole derivatives with high enantioselectivities and yields, regardless of the stereochemistry of the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Physical
Nilanjana Majumdar
Summary: Catalytic asymmetric transformation is a powerful strategy for synthesizing diverse nonracemic molecular entities. Carboxylic acids have been explored as building blocks in this area, and significant advancements have been made in the last three decades. They can act as both C- and O-nucleophiles, as well as electrophiles, in asymmetric reactions under catalytic conditions.
Review
Chemistry, Organic
Juliana Baptista Simoes, Daniel Leite da Silva, Sergio Antonio Fernandes, Angelo de Fatima
Summary: Calix[n]arenes are considered as versatile organocatalysts due to their adjustable three-dimensional molecular structure, easy synthesis, and compatibility with various reaction systems.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Applied
Helene Pellissier
Summary: This review updates the research in the field of enantioselective domino reactions promoted by chiral catalysts derived from first row metals, such as zinc, iron, copper, scandium, nickel, cobalt, titanium, chromium and magnesium, since the beginning of 2019. It illustrates the impressive range of novel highly enantioselective domino reactions that can be achieved with a diversity of these catalysts, providing a one-pot access to very complex and functionalized chiral molecules from simple starting materials.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
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, Physical
Xavier Abel-Snape, Gina Wycich, Mark Lautens
Summary: A palladium-catalyzed three-component domino reaction for accessing indene derivatives is described. The reaction involves the sequential formation of three bonds, with the first two resulting from inter- and intramolecular carbopalladation, and the final bond arising from an attack by a terminating nucleophilic reagent. The starting tether on the iodoarene can be modified to yield either indenes or benzofulvenes. Additionally, the use of an oxabicycle as an acetylene surrogate is demonstrated, and the enantioselective synthesis of indenes is preliminarily explored.
Article
Chemistry, Physical
Ningning Zhang, Zhiyong Sun, Changzhu Wu
Summary: The polymeric approach of combining proteins with organocatalytic polymers to generate artificial enzymes expands the applications of asymmetric organocatalysis and provides new avenues for combining proteins/enzymes with well-designed organocatalytic polymers for useful synthetic reactions.
Article
Chemistry, Multidisciplinary
Jian Cao, Ling Chen, Feng-Na Sun, Yu-Li Sun, Ke-Zhi Jiang, Ke-Fang Yang, Zheng Xu, Li-Wen Xu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
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, Organic
Shuai Shuai Huang, Zhan Jiang Zheng, Yu Ming Cui, Zheng Xu, Ke Fang Yang, Li Wen Xu
SYNTHESIS-STUTTGART
(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
Qiao-Ying Sun, Zhao Li, Zheng Xu, Zhan-Jiang Zheng, Jian Cao, Ke-Fang Yang, Yu-Ming Cui, Li-Wen Xu
CHEMICAL COMMUNICATIONS
(2019)
