Article
Chemistry, Multidisciplinary
D. Kortus, V. Eigner, P. Lhotak
Summary: The oxidation of 2,14-dithiacalix[4]arene led to the selective formation of S-spiro derivatives, indicating that the thiacalixarene fragment is more prone to spirocyclization than the calixarene one. Acid-induced rearrangement of the S-spiro compound resulted in a novel phenoxathiin-based calixarene macrocycle. The conformational preferences of these new inherently chiral macrocycles were studied using NMR spectroscopy, single-crystal X-ray analysis, and DFT calculations.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yueyao Chen, Jesse Ling, Angus B. Keto, Yun He, Kam-Hung Low, Elizabeth H. Krenske, Pauline Chiu
Summary: Epoxy and aziridinyl enolsilanes can react as oxyallylic cation equivalents in highly selective and stereoselective intramolecular (3+2) cycloadditions. Computational studies suggest that the stepwise reaction involves the conformational flexibility of the intermediate, which determines the formation of (3+2) cycloadducts. This method can be used for the synthesis of densely functionalized trans-hydrindane scaffolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Physical
Giulio Goti
Summary: This article discusses the application of catalytic radical methods in the functionalization of unsaturated carbohydrates, highlighting the opportunities they offer for new reaction design. These methods overcome the limitations of classical protocols and provide new routes for the synthesis of complex carbohydrates.
Article
Chemistry, Multidisciplinary
Narayanaswamy Jayaraman
Summary: Unsaturated monosaccharides expand the reactivity scope in sugars, leading to new methodologies, molecular structures, and functional entities. Endocyclic or exocyclic unsaturation as reactive moieties can lead to largely unknown structures through one carbon homologations. Molecular shifts and rearrangements allow interchanging reactivities from one carbon to another in unsaturated sugars, with activations of exocyclic unsaturated sugars offering newer possibilities to sugar chemistry reactions. Personal reflections stem from decades of explorations in unsaturated sugars from varied perspectives.
Review
Chemistry, Applied
Supriya Rej, Amrita Das, Tarun K. Panda
Summary: The hydroboration of alkynes is a significant method for synthesizing important vinylborane compounds, with implications for regioselectivity and stereoselectivity. Extensive studies have been conducted on catalytic conditions and mechanistic studies to selectively obtain a single isomer, aiming to provide readers with accurate knowledge of available catalytic systems for this reaction. Researchers are encouraged to explore new catalytic systems to achieve the remarkable process of hydroboration of alkynes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Tai-Ping Zhou, Fangrui Zhong, Yuzhou Wu, Rong-Zhen Liao
Summary: In this study, the reaction mechanism, regioselectivity, and stereoselectivity of the photochemical intramolecular [2 + 2] cycloaddition reaction catalyzed by a chiral thioxanthone molecule were investigated using quantum chemical calculations. The first C-C bond formation was identified as the rate-limiting and selectivity-controlling step, with the stereoselectivity being interaction-controlled. Moreover, the effects of catalyst substituents on the stereoselectivity of the photocycloadditions were explored, providing valuable mechanistic information for related photoinduced reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Jixiang Ni, Matteo Lanzi, Arjan W. Kleij
Summary: An unanticipated exo-cyclic nucleophilic attack of thiol reagents on vinyl cyclic carbonates is described, leading to the synthesis of allylic thioethers. This reaction pathway adds to the reactivity modes available for these heterocycles, complementing the previously reported endo-cyclic nucleophilic attack.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Chun-Chi Chen, Meng Dai, Lilan Zhang, Jing Zhao, Wei Zeng, Min Shi, Jian-Wen Huang, Weidong Liu, Rey-Ting Guo, Aitao Li
Summary: We investigated the mechanism of the P450tol enzyme from Rhodococcus coprophilus TC-2, which can hydroxylate toluene at the benzylic site. We solved the crystal structures of P450tol and its complex with the substrate, revealing how P450tol restricts the binding position of toluene and enables precise hydroxylation at the benzylic site. Additionally, we found that P450tol can also hydroxylate larger substrates and synthesized a self-sufficient chimeric enzyme with improved activity and stability. These findings highlight the potential of P450tol in biotechnological and pharmaceutical applications.
Review
Chemistry, Physical
Sahil Verma, Rahul Narayanlal Choudhary, Akash Prakash Kanadje, Uttam Chand Banerjee
Summary: Hydrolases, particularly lipases, play a significant role in the pharmaceutical industry by catalyzing the hydrolysis of ester bonds with high specificity and robustness, making them suitable for various organic synthesis procedures. Genetic engineering has further enhanced the catalytic capabilities of lipases, allowing for the development of customized enzymes for greener biocatalytic drug synthesis. Lipases may also play a key role in developing cascade reactions in organic synthesis, making them a promising candidate for future biocatalytic research in the pharmaceutical industry.
Article
Chemistry, Multidisciplinary
Andrea Dell'Acqua, Claas Schuenemann, Eszter Barath, Sergey Tin, Johannes G. de Vries
Summary: In this study, the hydroformylation and methoxycarbonylation of MVG were investigated to produce novel bifunctional monomers. Polyesters with high renewable-atom content were successfully prepared and characterized.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Kazuki Inaba, Yuna Naito, Mina Tachibana, Kazunobu Toshima, Daisuke Takahashi
Summary: A regioselective and beta-stereospecific d-/l-arabinofuranosylation method has been developed for efficient synthesis of biologically active natural glycosides. The method showed high regioselectivity and yield with complete beta-stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Yang Ke, Wei Li, Wenfeng Liu, Wangqing Kong
Summary: Scaffold diversity is crucial for the success of compound libraries in biological screening. This review focuses on recent efforts in Ni-catalyzed divergent and selective synthesis, which generate structurally diverse molecular scaffolds using the same substrate and varying the ligand backbone under almost identical reaction conditions. The progress achieved encourages the design and development of new selective catalytic systems and reveals new modes of catalytic transformation for broader synthetic applications.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Xinghua Zhang, Danna Lu, Zhenwei Wang
Summary: An efficient and green electrochemical method was described for alkyne difunctionalization without the use of oxidants. By using commercially available iodide radical and arylsulfonyl radical sources in an undivided electrochemical cell, a variety of (E)-beta-iodovinyl sulfones were obtained in one-pot with excellent regio- and stereoselectivity under mild and ecofriendly conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kler Huonnic, Bruno Linclau
Summary: This study reports high-yielding glycosidation and glycosylation reactions of 2,3-difluorinated- and 2,3,4-trifluorinated gluco- and galactopyranoside donors with a variety of acceptors under conventional trichloroacetimidate/TMSOTf activation, resulting in products with moderate to high anomeric selectivities. This methodology allows access to highly fluorinated glycans, as demonstrated by the synthesis of a pentafluorinated disaccharide.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Korkit Korvorapun, Yannick T. Boni, Thomas C. Maier, Armin Bauer, Thomas Licher, John E. Macor, Volker Derdau, Huw M. L. Davies
Summary: Rhodium-catalyzed C-H insertion by donor/acceptor carbenes is a useful transformation in organic synthesis, but the site-selectivity of the C-H transformation on the target molecule is often a major issue. Chiral rhodium carbene intermediates can achieve site-selective C-H functionalizations of challenging substrates such as N-aryl and N-heteroaryl piperidines, leading to the formation of highly stereoselective C-2 products. Additionally, N-aryl morpholines and piperazines can selectively react at the alpha position to the N-aryl group.
Article
Chemistry, Multidisciplinary
Cinzia Chiappe, Gian Carlo Demontis, Valeria Di Bussolo, Maria Jesus Rodriguez Douton, Francesco Rossella, Christian Silvio Pomelli, Stefania Sartini, Stefano Caporali
Article
Chemistry, Organic
Valeria Di Bussolo, Ileana Frau, Lucilla Favero, Vittorio Bordoni, Stefano Crotti, Gloria Uccello Barretta, Federica Balzano, Paolo Crotti
Article
Chemistry, Organic
Salvatore Princiotto, Valeria Di Bussolo, Vittorio Bordoni, Lucilla Favero, Stefano Crotti, Gloria Uccello Barretta, Federica Balzano, Paolo Crotti
Article
Chemistry, Organic
Francesco Berti, Andrea Menichetti, Valeria Di Bussolo, Lucilla Favero, Mauro Pineschi
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2018)
Article
Pharmacology & Pharmacy
Angela Fabiano, Anna Maria Piras, Gloria Uccello-Barretta, Federica Balzano, Andrea Cesari, Lara Testai, Valentina Citi, Ylenia Zambito
EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS
(2018)
Article
Chemistry, Multidisciplinary
Sofia Masi, Federica Aiello, Andrea Listorti, Federica Balzano, Davide Altamura, Cinzia Giannini, Rocco Caliandro, Gloria Uccello-Barretta, Aurora Rizzo, Silvia Colella
Article
Chemistry, Medicinal
Andrea Menichetti, Francesco Berti, Lorenzo Guazzelli, Lucilla Favero, Sebastiano Di Pietro, Gennaro Pescitelli, Mauro Pineschi
Article
Chemistry, Medicinal
Michela Vargiu, Lucilla Favero, Andrea Menichetti, Valeria Di Bussolo, Fabio Marchetti, Gennaro Pescitelli, Sebastiano Di Pietro, Mauro Pineschi
Article
Biochemistry & Molecular Biology
Felicia D'Andrea, Giulia Vagelli, Carlotta Granchi, Lorenzo Guazzelli, Tiziano Tuccinardi, Giulio Poli, Dalila Iacopini, Filippo Minutolo, Valeria Di Bussolo
Article
Chemistry, Organic
Valeria Di Bussolo, Salvatore Princiotto, Vittorio Bordoni, Elisa Martinelli, Lucilla Favero, Stefano Crotti, Gloria Uccello-Barretta, Federica Balzano, Mauro Pineschi, Paolo Crotti
Article
Biochemistry & Molecular Biology
Sebastiano Di Pietro, Dalila Iacopini, Aldo Moscardini, Ranieri Bizzarri, Mauro Pineschi, Valeria Di Bussolo, Giovanni Signore
Summary: This study introduces two new tris coumarin-dipicolinate europium (III) complexes, which can be tailored to be either mono or dual emitters and their properties tuned with simple chemical modifications. The research also reveals a rich chemical speciation in solution, which is studied in detail by paramagnetic NMR and emission spectroscopy.
Article
Chemistry, Multidisciplinary
Manuela Curcio, Alessandro Paoli, Giuseppe Cirillo, Sebastiano Di Pietro, Martina Forestiero, Francesca Giordano, Loredana Mauro, Diana Amantea, Valeria Di Bussolo, Fiore Pasquale Nicoletta, Francesca Iemma
Summary: This study successfully prepared new dual pH/redox-responsive nanoparticles with affinity for folate receptors, demonstrating potential applicability as a new drug vector in cancer therapy.
Article
Biochemistry & Molecular Biology
Lucilla Favero, Andrea Menichetti, Cosimo Boldrini, Lucrezia Margherita Comparini, Valeria Di Bussolo, Sebastiano Di Pietro, Mauro Pineschi
Summary: The study reveals the structural requirements and reaction conditions for regioselective nucleophilic addition reaction on alkyl aziridines using bis(pinacolate)diboron under copper catalysis. This is important for the preparation of functionalized beta-aminoboronates, which are key compounds in drug discovery.
Article
Chemistry, Organic
Lucrezia Margherita Comparini, Andrea Menichetti, Lucilla Favero, Sebastiano Di Pietro, Fabrizio Badalassi, Per Ryberg, Mauro Pineschi
Summary: The stereoselective reduction of a diastereoisomeric mixture of benzo[g]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselective installation of the three chiral centers present in the (3S,4aS,10aR)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[g]quinolines that are privileged structures in medicinal chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
