Article
Chemistry, Physical
Imre Kovacs, Ferenc Otvos, Arnold P. Farkas, Janos Kiss, Zoltan Konya
Summary: The adsorption, desorption and polymerization of acetaldehyde on the Rh(111) surface were investigated. It was found that acetaldehyde can polymerize on the surface, forming oligomers or longer polymers. The triple molecular mass species of acetaldehyde also exhibited interesting kinetic and thermodynamic features on the Rh(111) surface.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Review
Biochemistry & Molecular Biology
Kashaf Babar, Ameer Fawad Zahoor, Sajjad Ahmad, Rabia Akhtar
Summary: The synthesis of spirocyclic compounds has garnered attention from synthetic chemists for their privileged ring system and efficacy in drug discovery. Many natural compounds with spirocyclic moieties are effective in the pharmaceutical industry. Recent synthetic methodologies have been established for constructing various spirocompounds containing six-membered carbocycles/heterocycles.
MOLECULAR DIVERSITY
(2021)
Article
Polymer Science
Jasmine Sinha, Shafer Soars, Christopher N. Bowman
Summary: This article describes an efficient enamine organocatalyzed thiol-Michael click reaction and its broad application in cross-linking polymerizations. The nucleophilicity of the enamines used is crucial for the reaction efficiency and overall yields, with in situ formation of an enamine via photo-deprotection of an amine showing promising results in facilitating thiol-Michael reactions and improving functional group conversion rates.
Article
Chemistry, Multidisciplinary
Zubeda Begum, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano
Summary: Distinct boron fused primary amino amide organocatalysts were synthesized from commercially available amino acids. These catalysts showed good catalytic activities in asymmetric crossed aldol reaction, producing corresponding chiral anti-aldol adducts with high chemical yields, moderate diastereoselectivity, and good to excellent enantioselectivities (up to 94% yields, up to 90:10 dr, up to 94% ee).
Review
Chemistry, Multidisciplinary
Zhen-Wei Zhang, Shao-Wu Liu, Hong-Ping Huang, Yu-Hang Xie, Ruo-Chen Huang, Yan-Qiu Deng, Ning Lin
Summary: In this mini-review, we systematically analyze and reorganize the published literature on dehydroabietane-type bifunctional organocatalysts in the recent decade according to the type of catalysts. Our aim is for this review to provide helpful research information and serve as a foundation for further design and application of rosin-based organocatalysts.
Article
Chemistry, Organic
Ramarao Parella, Satish Jakkampudi, Pranjal Bora, Nagaraju Sakkani, John C. -G. Zhao
Summary: (English Summary:)
The study revealed that modularly designed organocatalysts (MDOs) can facilitate the domino Michael/Michael reaction with switchable enamine and iminium catalytic modes. By utilizing appropriate combinations of precatalyst modules and reaction conditions, both catalytic modes can be individually switched on and off. Under optimized conditions with both enamine and iminium catalysis modes activated, the desired domino reaction products can be obtained with good yields and stereoselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Miku Nomura, Zubeda Begum, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano
Summary: The catalytic functionality of new optically active thiourea fused gamma-amino alcohols was investigated in the asymmetric Mannich reaction. Chiral Mannich products, beta-amino keto compounds, with continuous chiral centers were obtained in excellent chemical yield (up to 88%) and stereoselectivities (up to syn : anti/93 : 7 dr, up to 99% ee), making them versatile synthetic intermediates for deriving various biologically active compounds.
Article
Chemistry, Multidisciplinary
Zubeda Begum, Haruka Sannabe, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano
Summary: Simple primary beta-amino alcohols act as efficient organocatalysts in the asymmetric Michael addition of beta-keto esters with nitroalkenes, producing highly pure chiral Michael adducts. The choice of catalyst and reaction temperature determines the enantiomeric outcome of the adducts.
Review
Chemistry, Multidisciplinary
Tapaswini Das, Seetaram Mohapatra, Asit Kumar Pradhan, Sabita Nayak
Summary: 3-Nitro-2H-chromene and its derivatives are important structural building blocks of many natural products and pharmacologically active compounds. The Michael/hetero-Michael addition reactions to 3-nitro-2H-chromene have been established as a vibrant and unique research area for constructing versatile 2H-chromene frameworks. In recent years, extensive exploration of efficient Michael donors has motivated the scientific community to work on these useful frameworks under various conditions.
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this study, a gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones was developed using an Al-Li-BINOL (ALB) complex catalyst. The reaction showed high diastereoselectivity with ratios up to 20:1 and enantioselectivity of 84-98% for various substrate combinations. This method is complementary to previous reports and improves selectivity for several chromones. Computational studies support the role of ALB as a bifunctional catalyst in this reaction and provide insights into the origin of the observed stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: A gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones, catalyzed by an Al-Li-BINOL (ALB) complex, was developed in this study. The diastereoselectivity reached 20:1 with 84-98% ee for various combinations of substrates. This protocol complements previous methods and improves selectivity for multiple chromones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Analytical
Qiuyue Wang, Zhao Li, Yitong Hao, Yuan Zhang, Chengxiao Zhang
Summary: This study synthesized a novel near-infrared fluorescent probe, Probe-ALDH, which shows great potential in drug discovery and cancer diagnosis by detecting and imaging aldehyde dehydrogenase.
ANALYTICAL CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Xin Huang, Wei Zhang
Summary: Organocatalysis offers unique activation modes, mild reaction conditions, and good catalyst adaptability, making it more efficient with the integration of green techniques. This article focuses on recyclable cinchona alkaloid-catalyzed reactions in the asymmetric synthesis of functionalized compounds of biological interest.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Viera Polackova, Dominika Kristofikova, Boglarka Nemethova, Renata Gorova, Maria Meciarova, Radovan Sebesta
Summary: Bifunctional N-sulfinylureas and thioureas with an appended pyrrolidine unit were synthesized and evaluated as organocatalysts in Michael additions. The N-sulfinyl-urea catalyst was more efficient than the corresponding thiourea, achieving up to 98% ee enantioselectivities for some substrates. The mode of action was elucidated through DFT calculations, confirming a dual activation mode involving enamine activation of aldehydes and hydrogen-bond activation of nitroalkenes.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Alessandro Brusa, Debora Iapadre, Maria Edith Casacchia, Alessio Carioscia, Giuliana Giorgianni, Giandomenico Magagnano, Fabio Pesciaioli, Armando Carlone
Summary: Asymmetric organocatalyzed multicomponent reactions are an important tool in organic synthesis for constructing complex scaffolds from simple starting materials. The Enders three-component cascade reaction was a cornerstone in this field, followed by numerous organocatalyzed cascade reactions. In this study, we successfully utilized acetaldehyde dimethyl acetal as a masked form of acetaldehyde in the Enders-type cascade reaction, allowing for the conversion of acetaldehyde, nitroalkenes, and enals into cyclohexenals with high stereochemical density and excellent enantioselectivity.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Analytical
Tamas Vermes, Mark Kielpinski, Thomas Henkel, Miquel A. Pericas, Esther Alza, Angelica Corcuera, Helmut Buschmann, Thomas Goldner, Andreas Urban
Summary: A new automated microfluidic screening assay has been developed in this study, allowing for the measurement of compound EC50 values in very short incubation times and the discrimination of different classes of CAMs. The system also revealed an intermediate CAM-N/A behavior in certain screening compounds.
ANALYTICAL METHODS
(2022)
Article
Chemistry, Multidisciplinary
Huixin Luo, Wei Tang, Hongyu Liu, Xiangmei Zeng, William Shu Ching Ngai, Rui Gao, Heyun Li, Ran Li, Huangtao Zheng, Jianting Guo, Fangfei Qin, Gang Wang, Kexin Li, Xinyuan Fan, Peng Zou, Peng R. Chen
Summary: The interactions between RNA and proteins are crucial for cellular processes. This study developed a photocatalytic crosslinking strategy combined with mass spectrometry and RNA sequencing to study the composition and dynamics of protein-RNA interactions. The approach identified numerous RNA binding proteins in human cells and investigated the dynamic changes of RBPs in macrophage cells and their interactions with SARS-CoV-2 RNA.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Maria Biosca, Pol de la Cruz-Sanchez, Daniel Tarr, Patricia Llanes, Erik A. Karlsson, Jessica Margalef, Oscar Pamies, Miquel A. Pericas, Montserrat Dieguez
Summary: A chiral phosphine-triazole ligand has been developed for the Ir-catalyzed asymmetric hydrogenation of exocyclic benzofused alkenes, which overcomes previous limitations and exhibits excellent enantioselectivity. The catalyst shows good tolerance towards various substituents and substitution patterns at both aromatic rings, making it an effective tool for hydrogenation of exocyclic olefins.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Leijie Zhou, Nicola Zanda, Moreshwar Chaudhari, Mariane Felicio Da Silva, Miquel A. . Pericas
Summary: A family of polystyrene-supported ligands based on the design of Defieber and Carreira were developed and successfully applied in the iridium-catalyzed asymmetric allylic amination of unmasked allylic alcohols, resulting in 27 examples with up to 99% enantiomeric excess. Two functional resins, L1 and L4, demonstrated significant advantages including easy preparation, ligand recyclability, and convenient handling for sequential use. Notably, the catalytic use of iridium complexes of L1 and L4 allowed for the efficient reuse of expensive iridium metal, which is not achievable under homogeneous conditions with monomeric complexes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Multidisciplinary
Xinyuan Fan, Peng R. Chen
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Physical
Manuel R. Rodriguez, Anabel M. Rodriguez, Sara Lopez-Resano, Miquel A. . Pericas, M. Mar Diaz-Requejo, Feliu Maseras, Pedro J. Perez
Summary: In the context of copper-catalyzed nitrene transfer to olefins, this study challenges the general assumption that the X ligand is displaced from the coordination sphere. Through experiments with well-defined copper(I) complexes, it is demonstrated that the catalytic and mechanistic behavior depends on the presence or absence of the chloride ligand bonded to the metal center, with different turnover-limiting steps.
Article
Chemistry, Organic
Nicola Zanda, Ludovica Primitivo, Moreshwar Chaudhari, Arjan W. Kleij, Miquel A. Pericas
Summary: A continuous flow organocatalytic synthesis of formamides has been developed using amines and CO2 reaction partners in the presence of a silane reductant. The process allows the preparation of a broad family of N-substituted formamides in good yield. The heterogenized catalyst and reductant have been optimized to achieve high productivity.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Fuhu Guo, Shiquan Shan, Xu Gong, Cancan Dai, Zhengjun Quan, Xiamin Cheng, Xinyuan Fan
Summary: We propose a novel and effective photocatalytic method for the methylation of & beta;-diketones with controllable degrees of deuterium incorporation by developing new methyl sources. By utilizing a methylamine-water system and a cascade assembly strategy, we synthesized methylated compounds with varying degrees of deuterium incorporation. This work demonstrates the utility of readily available reagents, methylamines and water, as a new methyl source, and provides a simple and efficient strategy for the synthesis of degree-controllable deuterium-labelled compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Arianna Brandolese, David H. Lamparelli, Miquel A. . Pericas, Arjan W. Kleij
Summary: A commercially available Lipase B from Candida antarctica immobilized onto a macroporous support (Novozym 435) was used as a benign oxidant for the epoxidation of various biorenewable terpenes in the presence of H2O2. The epoxidation protocol was explored under both heterogeneous batch and continuous flow conditions. The catalyst showed good recyclability under batch conditions for 10 cycles and could be used for more than 30 hours under continuous flow operation. This sustainable flow epoxidation allows for the production of gram quantities of terpene epoxides and the post-functionalization of biobased polymers.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Review
Chemistry, Multidisciplinary
Yanjun Liu, Yun Ge, Ruxin Zeng, William Shu, Ching Ngai, Xinyuan Fan, Peng R. Chen
Summary: Enzyme- and catalyst-generated reactive species have been utilized for covalently labeling biomolecules within a short range of a specific location in cells or at the cell-cell interface. These proximity labeling strategies, due to their high spatial resolution, have been combined with various bioanalytical techniques to study dynamic and complex biological processes. This review focuses on the development and applications of enzyme- and catalyst-triggered proximity chemistry for identifying protein interaction networks and cell-cell communications in living systems.
Article
Chemistry, Multidisciplinary
Xianrui Zhang, Haoran Huang, Yuan Liu, Zhigang Wu, Fengzhang Wang, Xinyuan Fan, Peng R. Chen, Jie Wang
Summary: Site-specific protein decaging by light is an effective approach for manipulating protein activities. A genetically encoded photocaged Asp was developed and used for the photocontrolled manipulation of various proteins, including firefly luciferase, kinases, and GTPase. This new tool may have broad applications for studying protein functions and biological processes in living cells.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Xianrui Zhang, Haoran Huang, Yuan Liu, Zhigang Wu, Fengzhang Wang, Xinyuan Fan, Peng R. Chen, Jie Wang
Summary: Site-specific protein decaging by light is an effective approach for manipulating protein activities in a gain-of-function manner. However, decaging strategy has not been extended to aspartic acid (Asp), an essential amino acid residue. We reported a genetically encoded photocaged Asp and demonstrated its application in manipulating various proteins as well as mimicking in situ phosphorylation events on kinases.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Xuan Liang, Shan Qian, Zhizheng Lou, Renming Hu, Yuchen Hou, Peng R. Chen, Xinyuan Fan
Summary: The development of a biocompatible photocatalytic technology termed CAT-NIR enables the spatiotemporal manipulation of biological processes in living animals using external near infrared light (NIR). This system utilizes Os(II) terpyridine complex as an efficient NIR photocatalyst for deboronative hydroxylation reactions, resulting in the release of bioactive molecules. CAT-NIR also allows for the regulation of affibody binding to cell surface receptors through genetic code expansion and computer-aided screening, providing a selective cell tagging technology with external NIR light.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Moreshwar B. Chaudhari, Prachi Gupta, Patricia Llanes, Leijie Zhou, Nicola Zanda, Miquel A. Pericas
Summary: In this study, the merging of polymer-supported asymmetric organocatalysis with continuous flow in a packed bed reactor was successfully used for the synthesis of indoloquinolizidines. A highly enantioselective, solvent-free and rapid conjugate addition reaction in continuous flow allowed the preparation of multigram amounts of relevant oxodiesters. The obtained Michael adducts were then used for the efficient diastereoselective synthesis of indoloquinolizidines through cascade Pictet-Splengler cyclisation-lactamisation in continuous flow. The conversion of enantiopure Michael adducts into delta-lactones via telescoped reduction/cyclisation in continuous flow was also explored.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Nicola Zanda, Leijie Zhou, Esther Alza, Arjan W. Kleij, Miquel A. Pericas
Summary: The article presents an efficient synthesis method using TBD catalyst to convert epoxy amines to 2-oxazolidone, combining the use of CO2 as a C-1 source and halide-free organocatalysis to continuously synthesize a series of heterocyclic products over a two-week period.
