Article
Chemistry, Organic
George Hutchinson, Carla Alamillo-Ferrer, Martin Fernandez-Pascual, Jordi Bures
Summary: The Nanjing Huamu Football Team has developed a number of outstanding players over the past 7 years and has made significant contributions to the local youth football movement.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Song Sun, Zhaobin Wang, Shijia Li, Cong Zhou, Lijuan Song, Hai Huang, Jianwei Sun
Summary: This study presents the first organocatalytic kinetic resolution of unactivated aziridines using sulfur nucleophiles, achieving excellent enantioselectivity. A chiral phosphoric acid was identified as an efficient catalyst for intermolecular ring opening under mild conditions, providing highly enantioenriched beta-amino thioethers and aziridines as useful synthetic building blocks.
Article
Multidisciplinary Sciences
Hui Zhou, Yu Zhou, Han Yong Bae, Markus Leutzsch, Yihang Li, Chandra Kanta De, Gui-Juan Cheng, Benjamin List
Summary: Enzymatic stereoselectivity is often better than most chemical catalysts in the conversion of small substrates. A recent study has reported the development of broadly applicable confined organocatalysts for the highly enantioselective cyanosilylation reaction. The selectivity (98:2 enantiomeric ratio) of the catalyst towards the pharmaceutically relevant product exceeds any other catalyst class, including engineered biocatalysts.
Article
Chemistry, Organic
Dmitri Trubitson, Jevgenija Martonova, Marina Kudrjasova, Kristin Erkman, Ivar Jarving, Tonis Kanger
Summary: An efficient enantioselective organocatalytic method has been developed for the synthesis of N-alkylated indoles with alpha-branched alkyl substituents from unsaturated indolyl ketones via a Michael addition. The resulting products exhibit high enantioselectivities and good yields, with tolerance towards various nucleophiles and substitution patterns of the indole ring. Both electron-withdrawing and electron-donating substituents can be accommodated at any position of the heteroaromatic ring.
Review
Chemistry, Applied
Andreu Vidal-Albalat, Bruno Matos Paz
Summary: Flavonoids and cannabinoids have been extensively studied for their therapeutic potential in various diseases. Creative synthetic methodologies have been developed to overcome limitations in their synthesis. This review provides an overview of enantioselective organocatalytic strategies applied to the synthesis of flavonoids and cannabinoids to date.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Masaaki Komatsuda, Ayane Suto, Hiroki Kondo, Hiroyuki Takada, Kenta Kato, Bunnai Saito, Junichiro Yamaguchi
Summary: This study presents a ring-opening fluorination of bicyclic azaarenes, leading to the construction of tertiary carbon-fluorine bonds. The protocol can be applied to a variety of bicyclic azaarenes and tolerate a range of functional groups. Mechanistic studies and enantioselective fluorination have also been explored.
Article
Chemistry, Organic
Maciej Majdecki, Piotr Grodek, Janusz Jurczak
Summary: In this study, an enantioselective phase transfer alpha-chlorination of beta-keto esters catalyzed by hybrid amide-based Cinchona derivatives was successfully reported. The reaction showed proper quantitative yields and high asymmetric induction, with use of only 0.5 mol % hybrid catalyst based on a Cinchona core allowing for highly enantioselective chlorination with various substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ji-Wei Ren, Zhen-Zhen Xie, Lan Zheng, Zhi-Peng Ye, Zhi-Xiong Deng, Qing-Lan Zhao, Jun-An Xiao, Kai Chen, Hao-Yue Xiang, Xiao-Qing Chen, Hua Yang
Summary: In this work, an organocatalytic enantioselective ring-reorganization domino sequence was established for the synthesis of pyrrolo[3,4-c]quinolinones with multiple chiral centers. The reaction showed high yields, excellent diastereoselectivities, and high enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Shaolei Xie, Zhi-Juan He, Ling-Hui Zhang, Bo-Lun Huang, Xiao-Wei Chen, Zong-Song Zhan, Fu-Min Zhang
Summary: Commercially available cinchona alkaloids have been developed to catalyze the enantiodivergent fluorination of beta-ketodiarylphosphine oxides for constructing carbon-fluorine quaternary stereocenters, showing broad substrate scope, excellent enantioselectivities, and scalability.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yuling Wu, Wu-Jingyun Zhou, Laiping Yao, Yadi Niu, Hongli Zhao, Cheng Peng, Bo Han, Wei Huang, Gu Zhan
Summary: In this study, an organocatalytic strategy for coupling aryl-naphthoquinones with thiosugars is reported, leading to the synthesis of axially chiral naphthoquinone thioglycoside with excellent stereoselectivity. Mechanistic studies showed the crucial role of H-bonding in stereochemical recognition. The reaction pathway involves atroposelective addition, followed by stereoretentive oxidation of the hydroquinone intermediate.
CHEMICAL COMMUNICATIONS
(2023)
Article
Multidisciplinary Sciences
Isabelle Nathalie-Marie Leibler, Makeda A. Tekle-Smith, Abigail G. Doyle
Summary: The study introduces a novel method using nucleophilic coupling partners through successive hydrogen atom transfer and oxidative radical-polar crossover. This strategy transforms C(sp(3))-H bonds into carbocations, enabling diverse bond formations with various nucleophiles and providing new site-selectivity for late-stage C(sp(3))-H functionalization.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Marta Meazza, Ramon Rios
Summary: This study describes the first synthesis of 2-alkenylquinolines from 2-allylquinolines and alpha,beta-unsaturated aldehydes. The reaction exhibits high regioselectivity and enantioselectivity, with a broad tolerance of functionalities in both the enal aromatic ring and the quinoline.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Thorsten Kinsinger, Uli Kazmaier
Summary: The Matteson homologation with vinyl nucleophiles is a versatile tool for synthesizing highly substituted and functionalized allyl boronic esters. It provides high yields and stereoselectivities, especially with sterically demanding alkyl boronic esters and/or Grignard reagents. This method has been successfully applied in the synthesis of the polyketide fragment of lagunamide B.
Article
Chemistry, Organic
Eider Dunabeitia, Aitor Landa, Rosa Lopez, Claudio Palomo
Summary: The study demonstrates the capability of bicyclic acylpyrrol lactims to act as pronucleophiles and form carbon-carbon bonds under organocatalytic conditions, leading to the synthesis of chiral pyrrolodiketopiperazines. The use of ureidoaminal-derived Bronsted bases in the Michael addition to nitroolefins allows for the generation of heterocyclic scaffolds with a high degree of skeletal diversity.
Article
Chemistry, Organic
Pavan Sudheer Akula, Yung-Ju Wang, Bor-Cherng Hong, Gene-Hsiang Lee, Su-Ying Chien
Summary: The organocatalytic alpha-alkylation of vinylogous carbonyl compounds to hydroxynitroolefins for the synthesis of hemiacetals was achieved with excellent enantioselectivities and high yields. The addition of Et3N led to high diastereoselectivity (>20:1). The alpha- and gamma-alkylation of vinylogous ketone against nitroolefins exhibited high but opposite facial selectivities, with the transformation of the hemiacetal products demonstrated to other polycyclic compounds, including the euroticin B analog.
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)