Article
Chemistry, Applied
Yushan Xiao, Yimin Jia, Jinfeng Huang, Xiangyu Li, Zhiwen Zhou, Jing Zhang, Mou Jiang, Xin Zhou, Zhong-Xing Jiang, Zhigang Yang
Summary: A metal-free direct trifluoromethylthiolation method has been established for the synthesis of SCF3-substituted sulfonium ylides, using sulfonium salt or alpha-bromoacetic ester as precursors. This method enables the construction of SCF3-substituted sulfonium ylides from a wide range of substrates, including ketones, esters, and PEGylated substrates. The application of this approach in large-scale preparation and the fluorescence and fluorine-19 magnetic resonance imaging capabilities of the product are also explored.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Akshay Subhash Narode, Rai-Shung Liu
Summary: A one-pot synthesis of 5,6-dihydroindolo[2,1-a]isoquinolines from gold-catalyzed annulations between N-(oalkynylphenyl)imines and alpha-diazo esters is described. This cascade reaction involves the attack of the diazo ester at the imine to form cis-aziridine, followed by stereoselective [3 + 3]-annulations with the tethered arylalkyne. This new catalysis has been utilized to prepare a bioactive molecule of 5,6-dihydroindolo[2,1-a]isoquinoline.
Article
Chemistry, Multidisciplinary
Sudip Baguli, Subham Sarkar, Soumajit Nath, Dibyendu Mallick, Debabrata Mukherjee
Summary: In this study, two thermally stable azomethine ylides were isolated, and it was found that they formed N-picoCAAC-CuCl complexes when reacted with CuCl. Computational analysis revealed that the pendant Npy and the softer nature of Cu(I) played crucial roles in this reaction. The resulting complexes can be used as highly active Rh(I) catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Arthur Lebrene, Thomas Martzel, Laura Gouriou, Morgane Sanselme, Vincent Levacher, Sylvain Oudeyer, Carlos Afonso, Corinne Loutelier-Bourhis, Jean-Francois Briere
Summary: A straightforward method for synthesizing original 1,6-diazabicyclo[4.3.0]nonane-2,7-diones was developed using a DBU-organocatalyzed multicomponent Knoevenagel-aza-Michael-Cyclocondensation reaction. Analysis of key reactive intermediates using mass spectrometry confirmed the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Chemistry, Applied
Jing Huang, Bo Jiang, Xiyuan Zhang, Yanfeng Gao, Xiufang Xu, Zhiwei Miao
Summary: A synthetic strategy for accessing functionalized azabicyclo[3.3.1]alkenones with three tertiary stereocenters has been developed. The method is scalable and the products can be transformed to various eight-membered-ring bridged heterocyclic molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Angelina Kazakova, Lyubov G. Rubicheva, Alexander S. Konev, Alexander F. Khlebnikov
Summary: The diastereoselective synthesis of PEGylated heterocycles in high yields was reported in this study. The stereocontrol of product configuration was achieved through the stereospecificity of two consecutive concerted reactions. Characterization of the resulting PEGylated heterocycles was exhaustively done by various spectroscopic techniques.
Article
Multidisciplinary Sciences
Li Li, Kun Deng, Yajie Xing, Cheng Ma, Shao-Fei Ni, Zhaofeng Wang, Yong Huang
Summary: This article reports the synthesis of a class of hypervalent iodine reagents with a transferrable sulfoxonium group, which can react with unsaturated bonds such as alkenes, alkynes, nitriles, and allenes to form sulfoxonium-containing cyclic structures.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Daisuke Sakamoto, Isabel Gay Sanchez, Jiri Rybacek, Jaroslav Vacek, Lucie Bednarova, Marketa Pazderkova, Radek Pohl, Ivana Cisarova, Irena G. Stara, Ivo Stary
Summary: This study describes an asymmetric synthesis method for the preparation of optically pure and conformationally locked oxabenzo[5]helicenes. These compounds can be transformed into cycloiridated organometallics and exhibit excellent catalytic performance in asymmetric transfer hydrogenation reactions.
Article
Chemistry, Multidisciplinary
Johannes Fessler, Kathrin Junge, Matthias Beller
Summary: An efficient and general cascade synthesis of pyrroles from nitroarenes using an acid-tolerant homogeneous iron catalyst is presented. The method involves initial (transfer) hydrogenation using an iron-Tetraphos catalyst and subsequent acid catalysed Paal-Knorr condensation. It shows high functional group tolerance, complementing reactivity, and enhanced chemoselectivity.
Article
Chemistry, Organic
Aliyaah J. M. Rahman, Lucie Finck, Wolfgang Obermayer, Martin Oestreich
Summary: The transition-metal-free protocol allows for the arylation of N-phenyl and N-benzoyl-substituted, benzaldehyde-derived imine derivatives with functionalized aryl pronucleophiles. Aryl nucleophiles are released from silicon protected aryl-substituted diazenes through desilylation with potassium trimethylsilanolate, simultaneously losing dinitrogen.
Review
Biochemistry & Molecular Biology
Hai-Lei Cui
Summary: DMSO, as a low-toxicity, inexpensive and easily accessible solvent, has been extensively used as a versatile reagent for the synthesis of functionalized molecules. The past decade has witnessed impressive achievements in the direct synthesis and modification of heterocyclic compounds using DMSO as a reagent.
Article
Chemistry, Organic
Agata Tyszka-Gumkowska, Janusz Jurczak
Summary: The reactivity of glycine ketimine ester with alpha, beta-unsaturated ketones was studied under high pressure conditions in the presence of macrocyclic hybrid phase-transfer catalysts. Control over the reactions was achieved by selecting appropriate conditions and specific orientation of hydrogen bond donors in the macrocyclic phase-transfer catalysts, resulting in high yields of up to 99% and excellent diastereoselectivity of >99:1.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Jianfeng Zheng, Lin Yang, Xin Dai, Lvli Chen, Luhao Tang, Yuqiao Zhou, Wei-Dong Z. Li
Summary: Magnesium-(II)-catalyzed cascade reactions of N,N'-cyclic azomethine imines with indolyl-substituted isocyanides were conducted. The method showed high tolerance towards different functional groups and had a wide range of substrates. A series of anti-pentacyclic spiroindolines with N,N'-fused heterocycle skeletons were obtained in good yields (up to 82%) with high selectivity (8.5:1 dr) under mild conditions. Interestingly, a sequential HOAc-mediated protonation led to diastereoenriched epimerization, resulting in the formation of exclusively syn-pentacyclic spiroindolines.
Article
Chemistry, Organic
Chao Shan, Jinping Xu, Liming Cao, Chaoming Liang, Ruihua Cheng, Xiantong Yao, Maolin Sun, Jinxing Ye
Summary: This study developed a practical continuous flow protocol for efficient synthesis of various functionalized piperidines within minutes, with high yields and enantiomeric excess. The scalability and utility of the process were demonstrated through the efficient synthesis of a drug precursor.
Article
Chemistry, Multidisciplinary
Aaron Gutierrez Collar, Cristina Trujillo, Bruce Lockett-Walters, Brendan Twamley, Stephen J. Connon
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Aaron Gutierrez Collar, Cristina Trujillo, Stephen J. Connon
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Umar Farid, Maria Luisa Aiello, Stephen J. Connon
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Simon N. Smith, Ryan Craig, Stephen J. Connon
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Simon P. Curran, Brendan J. Fallon, Stephen J. Connon
Article
Biochemistry & Molecular Biology
Claire Fergus, Mashael Al-Qasem, Michelle Cotter, Ciara M. McDonnell, Emiliano Sorrentino, Franciane Chevot, Karsten Hokamp, Mathias O. Senge, John M. Southern, Stephen J. Connon, Vincent P. Kelly
Summary: Base modification can occur throughout a transfer RNA molecule, with a particular emphasis on position 34 of the anticodon loop. Human enzymes can recognize a wide range of artificial derivatives for transfer RNA incorporation, while displaying strict specificity for decoding certain codons. Exploiting the queuosine incorporation pathway shows broad potential for intentionally engineering chemical diversity into transfer RNA anticodons.
NUCLEIC ACIDS RESEARCH
(2021)
Article
Chemistry, Organic
Mili Litvajova, Emiliano Sorrentino, Brendan Twamley, Stephen J. Connon
Summary: This study demonstrates the application of N-protected oxindole derivatives with unprecedented malleability in enantioselective phase-transfer-catalysed alkylations. By optimizing the structure of the catalyst, high levels of enantioselectivity were achieved. It was found that urea-based catalysts outperformed squaramide derivatives, and that installing a chlorine atom in the quinoline moiety of the catalyst improved reaction selectivity.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Simon N. Smith, Stephen J. Connon
Summary: The ring contraction-lactamisation of anhydrides with trimethylsilylazide in the presence of an amine catalyst has been studied. It is possible to generate 5,- 6- and 8-membered ring lactams from cyclic anhydrides under controlled conditions, with a simple operation procedure. Succinic anhydrides can be used to produce N-carboxyanhydrides for polymer chemistry and as beta-peptide precursors.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Cristina Trujillo, Sarah A. Cronin, Stephen J. Connon
Summary: A complete computational study was conducted to rationalize a new organocatalytic approach for the kinetic resolution of 4-substituted oxazinones, resulting in highly enantioenriched beta-amino acids. The study also investigated the alcoholytic kinetic resolution of a 7-memebered ring analogue for the first time, generating enantioenriched gamma-amino acids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Ciara M. McDonnell, Magda Ghanim, J. Mike Southern, Vincent P. Kelly, Stephen J. Connon
Summary: This study investigates the impact of modified beta-lysines on the growth rates of eubacterial cells. The results indicate that the observed effects are due to the post translational modification of Elongation Factor P (EFP) catalyzed by PoxA. The promiscuity of PoxA allows for examination of a wide range of exogenous beta-lysines.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Sarah A. Cronin, Stephen J. Connon
Summary: This study introduces a novel approach to catalytic, alcoholytic kinetic resolution of oxazinones using a stereochemically dense cinchona alkaloid-based catalyst. The catalyst enables highly enantiodiscriminatory ring-opening of oxazinones equipped with electrophilic aryl units, leading to the generation of orthogonally protected beta-amino acids for the first time.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Eoghan G. Delany, Stephen J. Connon
Summary: The enantioselective intermolecular crossed-benzoin condensation mediated by novel chiral N-heterocyclic carbenes derived from pyroglutamic acid has been investigated. Increasing both the steric requirement and the electron-withdrawing characteristics of the N-aryl ring led to more chemoselective, efficient and enantioselective chemistry. Subsequent protocol optimization involving o-substituted benzaldehyde as one reacting partner allowed a range of crossed-benzoins to be synthesized in moderate-good yields with moderate to excellent enantioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mashael A. Alqasem, Claire Fergus, J. Mike Southern, Stephen J. Connon, Vincent P. Kelly
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Amy C. Maguire, Vikas Kumar, Stephen J. Connon
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Bruce Lockett-Walters, Cristina Trujillo, Brendan Twamley, Stephen Connon
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)