Article
Chemistry, Organic
Wei Xie, Liang Zhao, Xinmei Fu, Rong Zhang, Xinyu Hao, Chunying Duan, Yaming Li
Summary: A new strategy for the synthesis of beta-amino alcohols and beta-amino ethers was developed, involving the three-component functionalization of olefins with sulfoxyimidoylsulfonium salt and a nucleophilic reagent using photoredox catalysis. The sulfoxyimidoylsulfonium salt plays a crucial role as the N-centred radical precursor. The strategy allows for the synthesis of beta-amino alcohols and beta-amino ethers with various functional groups in good yields under mild conditions, and offers the advantages of improved safety, no additives, and easy accessibility of raw materials.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Jing-Fei Wu, Nan-Wei Wan, Ying-Na Li, Qing-Ping Wang, Bao-Dong Cui, Wen-Yong Han, Yong-Zheng Chen
Summary: A dual-enzyme cascade strategy was developed for regiodivergent and stereoselective hydroxyazidation of alkenes, leading to the synthesis of various enantiomerically pure 1,2-azidoalcohols. This approach combines the asymmetric epoxidation of alkenes and regio-selective ring opening of epoxides with azide catalyzed by styrene monooxygenase and halohydrin dehalogenase. Additionally, a one-pot chemo-enzymatic route to chiral beta-hydroxytriazoles from alkenes was achieved by combining biocatalytic cascades and Cu-catalyzed azide-alkyne cycloaddition.
Article
Chemistry, Physical
Lia Martinez-Montero, Dirk Tischler, Philipp Suess, Anett Schallmey, Maurice C. R. Franssen, Frank Hollmann, Caroline E. Paul
Summary: A biocatalytic cascade was developed for the synthesis of enantioenriched azido alcohols, introducing chiral substituents through enzymatic epoxidation and regioselective cleavage reactions, leading to highly enantioenriched aromatic azido alcohols. This approach demonstrates the potential for practical production of these chiral compounds using two-component flavoprotein monooxygenases.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Saket Jain, Saurabh Sandip Satpute, Raushan Kumar Jha, Mili Sanjeev Patel, Sangit Kumar
Summary: A new series of unsymmetrical phenyl tellurides derived from 2-N-(quinolin-8-yl) benzamide ligand has been synthesized by a copper-catalyzed method. These compounds have been transformed into corresponding unsymmetrical 2-N-(quinolin-8-yl)benzamide tellurium cations in order to enhance their Lewis acidity. These Lewis acidic tellurium cations have shown catalytic activities in the synthesis of substituted 1,2-dihydroquinolines and beta-amino alcohols under mild conditions. Mechanistic studies suggest that the enhanced Lewis acidity of tellurium center is responsible for these efficient catalytic activities.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Kaushik Misra, Bipasa Halder, Flora Banerjee, Gourhari Jana, Himadri Sekhar Maity, Aditya Balasaheb Kachave, Ahindra Nag
Summary: A simple, new, and cost-efficient alternative route has been developed for the synthesis of unique beta-amino alcohols from a new type of 1,2-disubstituted styrene epoxides via a greener approach. Computational studies based on density functional theory (DFT) were conducted to investigate the mechanistic pathway for the formation of acetylated amino alcohols, which is the key step in the synthesis of beta-amino alcohols.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Multidisciplinary
Christopher J. J. Hall, William R. F. Goundry, Timothy J. Donohoe
Summary: Enantiopure 1,2-amino alcohols derived from abundant amino acids were used in C-C bond-forming hydrogen-borrowing alkylation reactions for the first time. The use of Ph*COMe aryl ketone facilitated the reactions, preventing racemisation of the amine stereocentre. The Ph* and trityl groups could be easily cleaved in one pot to give GABA products without further purification, allowing the two steps to be performed in sequence without isolation of the hydrogen-borrowing intermediate, eliminating the need for column chromatography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Cai Gao, Jiahao Zeng, Xianming Zhang, Yanzhi Liu, Zhuang-Ping Zhan
Summary: We developed a new photo-sensitizer, 2,4,5,6-tetrakis(2,7-dibromo-9H-carbazol-9-yl)isophthalonitrile (2,7-Br-4CzIPN), for the energy-transfer-driven N-O bond dissociation of oxime esters. In the presence of 2,7-Br-4CzIPN, difunctionalization of alkenes with oxime esters, including oxyimination, amino-carboxylation, and amidylimination, could afford versatile molecules with good yields and excellent regioselectivity, which are commonly found in natural products and drugs. Theoretical investigations and experiments have confirmed that 2,7-Br-4CzIPN possesses unique photophysical properties, suitable triplet energy, and outstanding photocatalytic activity.
Article
Biochemistry & Molecular Biology
Claudia Teixeira, Renato B. Pereira, Nuno F. S. Pinto, Catarina M. M. Coelho, Maria Jose G. Fernandes, Antonio G. Fortes, Maria S. T. Goncalves, David M. Pereira
Summary: Eugenol, the main component of clove essential oil, has shown anticancer activity. By synthesizing a series of derivatives and testing them, three compounds were found to have significant anticancer activity without toxicity towards noncancer cells.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Review
Chemistry, Multidisciplinary
Leah Fuhrman Javitt, Sofia Curland, Isabelle Weissbuch, David Ehre, Meir Lahav, Igor Lubomirsky
Summary: The ability to control the icing temperature of supercooled water (SCW) is of supreme importance in subfields of pure and applied sciences. In this Account, it is demonstrated that heterogeneous electrofreezing of SCW is a chemical process influenced by an electric field and specific ions, by capitalizing on the properties of polar crystals.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Organic
Michael B. Elbaum, Mahmoud A. Elkhalifa, Gary A. Molander, David M. Chenoweth
Summary: Forging new C(sp(3))-C(sp(3)) bonds to central positions within a peptide backbone is achieved by using electron-donor-acceptor complexes between Hantzsch ester and on-resin peptide N-hydroxyphthalimide radical precursors. The feasibility of this method is demonstrated through two-carbon homologations and homologation cyclizations of Atosiban and RGDf.
Article
Chemistry, Multidisciplinary
Daniya Aynetdinova, Reece Jacques, Kirsten E. Christensen, Timothy J. Donohoe
Summary: The use of benzylic and allylic alcohols in HFIP solvent with Ti((OPr)-Pr-i)(4) triggers a highly stereoselective polyene cyclisation cascade, forming three new carbon-carbon bonds and controlling the stereochemistry of up to five new stereogenic centers. The reaction is efficient, tolerates various functional groups, and generates water as a stoichiometric by-product. It employs a new polyene substrate-class and further research suggests a stereoconvergent mechanism. The products can be used for the synthesis of steroid-analogues in a single step.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Meera A. Shah, Ibrahim Khalil, Sofia Tallarico, T. Donckels, Pierre Eloy, Damien P. Debecker, Manuela Oliverio, Michiel Dusselier
Summary: In this work, the synthesis of alanine from lactic acid using ammonia and Ru/zeolite catalysts was investigated. High alanine selectivity was achieved with Ru/BEA catalyst, and reaction conditions were further optimized to improve turnover numbers and reduce catalyst leaching. However, the stability of the catalyst remains a concern.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Mahmoud Elkhalifa, Michael B. Elbaum, David M. Chenoweth, Gary A. Molander
Summary: This research demonstrates the compatibility of photochemistry with solid-phase peptide synthesis, using photochemical hydroalkylation to form C(sp(3))-C(sp(3)) bonds on resin. High yields were achieved using iridium-based photocatalysts and Hantszch ester, with full conversions within 30 minutes under ambient conditions. The chemistry is compatible with a broad range of peptide side chains, redox-active esters, and resin, representing the first example of photochemical peptide modifications on resin.
Article
Chemistry, Physical
Angappan Mano Priya, Basheer Aazaad, Divya Mariyam Biju
Summary: Norepinephrine plays a significant role in various bodily functions and behaviors, such as attention, cognitive function, stress reactions, and pain reactions. This study investigates the active role of amino acids and alcohols in mimicking the effects of norepinephrine through hydrogen bond interactions. It was found that alanine and methanol exhibit stronger interactions with norepinephrine compared to glycine and ethanol. This study sheds light on the biological importance and chemical behavior of norepinephrine in the presence of amino acids and alcohols.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Irena Dokli, Nevena Milcic, Petra Marin, Marina Svetec Miklenic, Martina Sudar, Lixia Tang, Zvjezdana Findrik Blazevic, Maja Majeric Elenkov
Summary: The kinetic resolution of a series of fluorinated styrene oxide derivatives using halohydrin dehalogenase was studied. A mutant HheC-W249P showed excellent enantioselectivity in catalyzing nucleophilic ring-opening reactions with azide and cyanide ions, yielding various enantiopure beta-substituted alcohols and epoxides. The enzyme demonstrated tolerance to substrates at concentrations over 50 mM, but different side reactions were observed at elevated concentrations and prolonged reaction times. Bio-catalytic azidolysis and cyanolysis of racemic 4-trifluoromethylstyrene oxide on a preparative scale resulted in the production of specific enantiomers with high yields and enantiomeric excesses.
CATALYSIS COMMUNICATIONS
(2021)
Review
Chemistry, Physical
Nicola Scotti, Filippo Bossola, Federica Zaccheria, Nicoletta Ravasio
Review
Chemistry, Physical
Denise Cavuoto, Federica Zaccheria, Nicoletta Ravasio
Article
Green & Sustainable Science & Technology
Emily Overturf, Simon Pezzutto, Martina Boschiero, Nicoletta Ravasio, Achille Monegato
Summary: Coffee silverskin is a major byproduct of coffee roasting in Italy, with the potential to be utilized as a substitute for raw materials to produce paper pulp, reducing environmental impact and greenhouse gas emissions in paper production. The study demonstrates the feasibility of incorporating CSS into paper production as part of a circular economy approach.
Article
Chemistry, Physical
Denise Cavuoto, Nicoletta Ravasio, Nicola Scotti, Antonella Gervasini, Sebastiano Campisi, Marcello Marelli, Giuseppe Cappelletti, Federica Zaccheria
Summary: A new process using cyclopentyl methyl ether as solvent for the selective hydrogenation of gamma-valerolactone to 1,4-pentanediol has been established, which was found to be influenced by the wettability of the silica support affecting the dispersion of copper catalyst and its activity.
MOLECULAR CATALYSIS
(2021)
Article
Polymer Science
Fabio Bertini, Adriano Vignali, Marcello Marelli, Nicoletta Ravasio, Federica Zaccheria
Summary: This study focuses on the preparation of styrene-free thermosetting resins using vegetable oils and terpenic comonomers, which not only addresses environmental and safety concerns but also allows for tunable physical properties. The potential applications of these resins in combination with natural fibers have also been explored.
Article
Chemistry, Physical
Marcello Marelli, Federica Zaccheria, Nicoletta Ravasio, Emanuela Pitzalis, Youcef Didi, Anne Galarneau, Nicola Scotti, Claudio Evangelisti
Summary: A simple and reproducible method called flow chemisorption hydrolysis (flow-CH) was reported for the synthesis of Cu-based heterogeneous catalysts.The method enabled the synthesis of size-controlled CuO nanoparticles (mean diameter 2.9 nm) that are homogeneously dispersed into meso-/macroporous silica monoliths.The CuO@SiO2-MN catalysts exhibited remarkable activity and high selectivity in the styrene oxide ring opening reaction under continuous flow-through conditions, surpassing the performance of previously reported CuO/SiO2 catalysts.
Article
Biochemistry & Molecular Biology
Valeria Pappalardo, Nicoletta Ravasio, Ermelinda Falletta, Maria Cristina De Rosa, Federica Zaccheria
Summary: Chlorogenic acid (CGA), a natural antioxidant widely found in plants, can be converted to lipophilic esters through a non-enzymatic catalytic process. By using sulfonic resins under solvent-free conditions, a series of esters with yields up to 93% can be obtained via the reaction of CGA with fatty alcohols of different chain lengths. This one-step reaction can be carried out under mild conditions, achieving conversions up to 96% and selectivity up to 99%. The esters obtained were fully characterized and showed increased antioxidant activity compared to the parent acid and butylated hydroxyanisole. In-silico testing also indicated their low toxicity. The increased lipophilicity of the esters allows for their formulation in cosmetic and nutraceutical lipid-based products.
Review
Chemistry, Physical
Denise Cavuoto, Leandro Ardemani, Nicoletta Ravasio, Federica Zaccheria, Nicola Scotti
Summary: Levulinic acid and its esters can be produced extensively in biobased industries through consolidated industrial processes, playing a central role in the circular economy. Copper-based heterogeneous catalysts have been used for the transformation of levulinic acid and esters with hydrogen, providing a more cost-effective and environmentally friendly alternative to the traditional noble metal catalysts. This critical review aims to provide a comprehensive overview of the research advancements in the past decade in this field.
Article
Chemistry, Multidisciplinary
Nicola Scotti, Nicoletta Ravasio, Federica Zaccheria, Adrian Irimescu, Simona Silvia Merola
