Article
Chemistry, Multidisciplinary
Donglei Wang, Ying-Bo Shao, Yunrong Chen, Xiao-Song Xue, Xiaoyu Yang
Summary: An efficient method for the asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been developed using chiral phosphoric acid catalysis for enantioselective electrophilic aromatic aminations with azodicarboxylates. This method allows for the synthesis of a wide range of chiral macrocycles with varying ring sizes and functional groups, achieving high yields and enantioselectivities. The mechanism and origins of the stereoselectivities of these reactions were investigated through experimental studies and computational calculations. Preliminary utilization of the planar-chiral macrocycle as a chiral organocatalyst demonstrated the potential applications of these novel chiral skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chenxiao Qian, Pengfei Li, Jianwei Sun
Summary: A catalytic enantioselective variant of oxidative rearrangement of indoles to access oxindoles has been developed using chiral phosphoric acid catalysis, providing a rapid access to a range of enantioenriched spirooxindoles with high enantioselectivity controlled by dynamic kinetic resolution.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Elisa Brambilla, Camilla Pozza, Silvia Rizzato, Giorgio Abbiati, Valentina Pirovano
Summary: This paper describes an enantioselective phosphine-catalyzed [3+2] cycloaddition reaction between aza-aurones and allenoates. The reaction proceeds under mild conditions and offers 2-spirocyclopentyl indolin-3-one derivatives as a single gamma-isomer with high stereocontrol.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Vasco Corti, Mathias Kirk Thaegersen, Valdemar Juel Enemaerke, Nomaan M. Rezayee, Casper L. Barlose, Karl Anker Jorgensen
Summary: The first atroposelective aminocatalytic methodology for the construction of C-N atropisomers is described. By directly coupling indole-2-carboxaldehydes to ortho-quinones, a new library of functionalized and enantioenriched C-N atropisomers was obtained using a designed and synthesized aminocatalyst. The synthetic utility of these atropisomers was demonstrated through various transformations.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Tao Wang, Bo Huang, You-Qing Wang
Summary: Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3-methylene isoindolinone and in situ-generated ortho-quinone methide substrates is achieved. This reaction allows the construction of spiro chroman-isoindolinones containing spiro-N,O-heterocycles with high enantioselectivity, with a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Avene C. Colgan, Rupert S. J. Proctor, David C. Gibson, Padon Chuentragool, Antti S. K. Lahdenpera, Kristaps Ermanis, Robert J. Phipps
Summary: This study reports a significant advancement in the catalytic enantioselective Minisci reaction, allowing the use of α-hydroxy radical coupling partners to obtain valuable enantioenriched secondary alcohol products. The approach is highly regioselective as well as highly enantioselective.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Suman K. Saha, Anupriya Bera, Soniya Singh, Nirmal K. Rana
Summary: Nitrogen-containing heterocyclic compounds have been extensively studied for their significant applications in synthetic organic chemistry, agrochemicals, and pharmaceuticals. alpha,beta-Unsaturated imines or conjugated imines have been found to react with a versatile family of compounds, leading to the synthesis of important cyclic and acyclic products. This review highlights the recent advances in enantioselective reactions of alpha,beta-unsaturated imines and their synthetic methodologies for synthesizing nitrogen-containing heterocycles containing four to six-membered rings. Additionally, the synthesis of rarely found seven, eight, and nine-membered nitrogen-containing heterocycles is also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ryuichi Nishiyori, Megumi Okada, John R. J. Maynard, Seiji Shirakawa
Summary: This study demonstrated the successful development of highly enantioselective bromolactonizations of 4-aryl-4-pentenoic acids using BINOL-derived chiral bifunctional sulfide catalysts, highlighting the importance of the bifunctional design in chiral sulfide catalysts. The catalytic asymmetric reaction system could also be applied to highly stereoselective desymmetrizing bromolactonizations, showing promising potential for further applications in asymmetric synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Editorial Material
Chemistry, Physical
Svetlana B. Tsogoeva, Guangbin Dong, Lutz Ackermann
Summary: This Special Collection discusses the latest strategies and progress in ring synthesis, including catalytic domino reactions and one-pot processes. Contributions cover transition-metal catalysis, organocatalysis, nanocatalysis, and photoredox catalysis for preparing carbocyclic and heterocyclic compounds.
Article
Chemistry, Organic
Xuebo Gao, Rong Chang, Junxin Rao, Danyang Hao, Zhuxia Zhang, Cong-Ying Zhou, Zhen Guo
Summary: Here, we report a halogen-bonding-based electron donor-acceptor (EDA) complex-promoted photoreaction for the synthesis of C2-malonylated indoles. The protocol allows for the efficient coupling of indoles with diethyl bromomalonate under visible-light irradiation without the need for any transition-metal catalyst or photocatalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Nobuya Tsuji, Pavel Sidorov, Chendan Zhu, Yuuya Nagata, Timur Gimadiev, Alexandre Varnek, Benjamin List
Summary: Catalyst optimization processes often rely on qualitative assumptions of chemists based on screening data, while machine learning models using molecular properties or calculated 3D structures are time-consuming and costly. This study proposes a machine learning model based on fragment descriptors, which are fine-tuned for asymmetric catalysis and result in robust and efficient virtual screening. Through theoretical design and experimental validation, new catalysts with higher selectivities in a challenging synthesis were developed using only moderately selective training data.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Antonia Di Mola, Felice De Piano, Lorenzo Serusi, Giovanni Pierri, Laura Palombi, Antonio Massa
Summary: The investigation of the reactivity of an alpha-amido sulfone derived from 2-formyl benzoate under organocatalytic conditions in the presence of acetylacetone allowed the synthesis of a new heterocyclic hybrid isoindolinone-pyrazole with high enantiomeric excess. Dibenzylamine was also used as a nucleophile to afford an isoindolinone with aminal substituent in 3-position in suitable selectivity. The use of Takemoto's bifunctional organocatalyst not only led to observed enantioselectivity but was also important in accomplishing the cyclization step in both cases. Notably, this catalytic system proved to be particularly effective in comparison to widely used phase transfer catalysts.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Bedrich Formanek, Vit Seferna, Marta Meazza, Ramon Rios, Mahendra Patil, Jan Vesely
Summary: This study reports the organocatalytic amination of pyrazol-5-ones with azodicarboxylates catalyzed by quinine, yielding enantiomerically enriched hydrazine adducts with quaternary stereocenters in high yields and enantioselectivities. Theoretical calculations help propose the relationship between the quinine catalyst and reactants, explaining the observed stereochemical outcome and trends in reaction effectiveness.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tianjiao Cui, Chen-Xi Ye, Jordan Thelemann, Daniel Jenisch, Eric Meggers
Summary: Enantioselective or enantioconvergent iron-catalyzed ring-closing C(sp(3))-H aminations of N-aroyloxyurea through intermediate iron nitrene species provide chiral 2-imidazolidinones in high yield and with excellent enantioselectivity (up to 99% yield and 95% ee in 40 examples). This is a rare case of combining sustainable iron catalysis with C(sp(3))-H amination and asymmetric catalysis. Chiral 2-imidazolidinones are commonly found in bioactive molecules and can be hydrolyzed to valuable chiral vicinal diamines in a single step.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Duanyang Kong, Maxime Munch, Qiqige Qiqige, Christopher J. C. Cooze, Benjamin H. Rotstein, Rylan J. Lundgren
Summary: Carbazole/cyanobenzene photocatalysts have been shown to promote direct isotopic carboxylate exchange of C(sp(3)) acids with labeled CO2, allowing for isotopic incorporation of substrates that are not compatible with traditional transition-metal-catalyzed degradation-reconstruction approaches or prone to thermally induced reversible decarboxylation at room temperature in short reaction times. The radiolabeling of drug molecules and precursors with [C-11]CO2 has been successfully demonstrated.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Oncology
Hoi-Wing Leung, Carmen Oi Ning Leung, Eunice Y. Lau, Katherine Po Sin Chung, Etienne H. Mok, Martina Mang Leng Lei, Rainbow Wing Hei Leung, Man Tong, Vincent W. Keng, Cong Ma, Qian Zhao, Irene Oi Lin Ng, Stephanie Ma, Terence K. Lee
Summary: This study identified a EPHB2/beta-catenin/TCF1 positive feedback loop that enhances cancer stemness and sorafenib resistance in HCC, providing a targetable axis to combat acquired drug resistance in HCC.
Article
Chemistry, Medicinal
Jiqing Ye, Lin Lin, Jinyi Xu, Paul Kay-sheung Chan, Xiao Yang, Cong Ma
Summary: Oseltamivir is a successful neuraminidase inhibitor in current anti-influenza therapy, and novel derivatives with pyrazole moiety show promising activity against NA. ADME evaluation indicates these derivatives have drug-like properties with better oral absorption and cell permeability compared to Oseltamivir carboxylate. Molecular docking studies confirm the interaction between the derivatives and NA enzyme active site as well as 150-cavity, providing valuable information for further optimization.
Article
Chemistry, Multidisciplinary
Christopher J. C. Cooze, Wesley McNutt, Markus D. Schoetz, Bohdan Sosunovych, Svetlana Grigoryan, Rylan J. Lundgren
Summary: Metal-catalyzed enantioselective conjugate additions are reliable methods for stereoselective synthesis, but multicomponent reactions initiated by conjugate arylation of acyclic pi-systems are rare. This study demonstrates a new Rh-catalyst system that allows highly enantioselective conjugate addition reactions of electron-deficient 1,3-dienes, generating Z-homoallylic alcohols with three stereocenters. The reaction products exhibit high diastereoselectivity and optical purity, enabling the synthesis of compounds with multiple stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Long Yin Lam, Cong Ma
Summary: A Chan-Lam-type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in high yields with the presence of a copper catalyst and potassium sulfite. The mechanistic study revealed that potassium sulfite was involved in the deoxygenation of sulfinates through a radical process.
Article
Chemistry, Multidisciplinary
Michael G. J. Doyle, Alexis L. Gabbey, Wesley McNutt, Rylan J. Lundgren
Summary: In this study, electron-deficient arylacetates were utilized as benzyl nucleophile surrogates to successfully generate enantioenriched acyclic molecules containing quaternary carbon centers via a two-step substitution-decarboxylation process. Products were often obtained with >90% ee using a commercially available catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Microbiology
Renee W. Y. Chan, Kin P. Tao, Jiqing Ye, Kevin K. Y. Lui, Xiao Yang, Cong Ma, Paul K. S. Chan
Summary: Influenza virus is a major public health challenge characterized by high morbidity and mortality. Oseltamivir is commonly used as an antiviral, but resistant strains have been detected. This study designed and synthesized two new compounds that showed significant antiviral activity against both seasonal and oseltamivir-resistant strains. These compounds have the potential to be an important addition to the arsenal of antiviral drugs.
Article
Biochemistry & Molecular Biology
Jiqing Ye, Xiao Yang, Cong Ma
Summary: Streptococci are bacteria that significantly impact human and livestock health, and the emergence of antimicrobial resistance has created an urgent need for new antimicrobial agents. In this study, a class of compounds called sigmacidins were discovered to have excellent antimicrobial activity against Streptococci. A combination of computational methods was used to gain insight into the mechanism of action and structural basis of sigmacidins as antimicrobials, providing new directions for further optimization.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Duanyang Kong, Qiqige Qiqige, Wesley McNutt, Rocco Paciello, Ansgar Schaefer, Mathias Schelwies, Rylan J. Lundgren
Summary: Transition metal catalyzed hydrogenation of alkenes is a widely used technology in both laboratory and chemical industry settings. In this study, a selective mono-hydrogenation of electron-poor substrates was achieved using specific Rh(CO)(2)acac/xantphos based catalysts. This finding is significant for the design of related hydrogenation processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Yangyi Qiu, Adrian Jun Chu, Tsz Fung Tsang, Yingbo Zheng, Nga Man Lam, Kendra Sek Lam Li, Margaret Ip, Xiao Yang, Cong Ma
Summary: A series of new derivative inhibitors with good antimicrobial activity against clinically significant pathogens were discovered in this study. Compound 22r exhibited the best antimicrobial activity with the lowest inhibitory concentration against diverse bacteria.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Long Yin Lam, King Hong Chan, Cong Ma
Summary: Functionalized aryl sulfonamides are important building blocks in pharmaceutical industry. This study developed a one-step synthesis method using stable solid commodity chemicals in various solvents, and demonstrated tolerance towards diverse functional groups commonly present in medicines and drug intermediates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Jiqing Ye, Xiao Yang, Cong Ma
Summary: Staphylococcus aureus is a common pathogen that causes infectious diseases, including drug-resistant strains. The study developed a ligand-based workflow to identify potential antimicrobials against S. aureus by targeting bacterial transcription. Four compounds were identified as potential antimicrobials, with strong binding affinity to NusB.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Qiqige Qiqige, Rylan J. Lundgren, Duanyang Kong
Summary: Stereodivergent dual catalysis is a powerful tool for selectively preparing four stereoisomers from molecules with two chiral centers. However, generating molecules with three newly formed stereocenters using dual catalyst approaches remains challenging.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Michael G. J. Doyle, Rylan J. Lundgren
Summary: The Cu-catalyzed oxidative cross-coupling of N- and O-nucleophiles with aryl boronic acids (the Chan-Lam reaction) is a valuable method for preparing aniline and phenol derivatives, with high chemoselectivity and mild reaction conditions. In addition, we have developed the analogous carbon-carbon bond forming variant for the first time.
CHEMICAL COMMUNICATIONS
(2021)
Article
Multidisciplinary Sciences
Yangyi Qiu, Cong Ma
