Article
Chemistry, Organic
Nai-Chen Hsueh, Meng-Yang Chang
Summary: We describe a facile-operational, high-yield method for the diastereocontrolled preparation of novel sulfonyl benzofused fluorooxabicyclo[4.2.1]nonanes by a straightforward synthetic route, including the reduction and intramolecular nucleophilic fluorocyclization. This method allows for the installation of a fluoro-atom on the bridged head position in a short time and under mild conditions, resulting in the formation of one carbon-carbon and one carbon-fluorine bond.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Rofin Mangali, Sengodagounder Muthusamy
Summary: This study demonstrates the BF3-catalyzed S-H insertion reactions of alpha-diazo imidamides and various substituted thioureas/thiosemicarbazones/cyclic thioamides to afford the corresponding S-H insertion products. The method exhibits wide substrate applicability and resistance to moisture and air, with moderate to excellent yields.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Sengodagounder Muthusamy, Ammasi Prabu
Summary: A new synthetic method has been developed for the highly chemoselective cleavage of enones using BF3·OEt2 catalyst under transition metal-free conditions, leading to the synthesis of 3-alkylated oxindoles. This method demonstrates good functional group tolerance and broad substrate scope.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Physical
Paul M. DeMent, Chenlu Liu, Joseph Wakpal, Richard N. Schaugaard, H. Bernhard Schlegel, Hien M. Nguyen
Summary: Phenanthroline is a commonly used bidentate ligand in coordination chemistry, which can be tuned to develop efficient and stereoselective catalysts. By activating 2-deoxy-2-fluoro glycosyl halides with phenanthroline-based catalysts, glycosylations with high levels of alpha-selectivities and moderate to high yields can be achieved. The proposed mechanism for this catalytic glycosylation system involves double S(N)2 displacement pathways with phenanthroline catalysts, ensuring stereoselective formation of alpha-1,2-cis-2-fluoro glycosides.
Article
Chemistry, Organic
Kaizhi Li, Yixin Lu
Summary: Enantioselective gamma-addition of readily available alpha-substituted nitroacetates to allenoates has been achieved, providing a straightforward asymmetric synthesis of optically enriched alpha,alpha-disubstituted alpha-amino acid precursors. The reaction proceeds efficiently with high yields and good to excellent enantioselectivities in the presence of amino acid-derived phosphine catalysts, forming products containing a tetra-substituted stereogenic center.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Ao Sun, Zipeng Li, Yuchao Wang, Shuai Meng, Xiao Zhang, Xiangbao Meng, Shuchun Li, Zhongtang Li, Zhongjun Li
Summary: This study presents an indirect method for the stereoselective synthesis of alpha-Kdo glycosides. The method utilizes a C3-p-tolylthio-substituted Kdo phosphite donor to achieve enhanced reactivity and complete alpha-stereocontrol. Various Kdo alpha-glycosides were successfully synthesized using this method. The orthogonality of the phosphite donor and thioglycoside donor was demonstrated through the one-pot synthesis of a trisaccharide. Furthermore, an efficient total synthesis route for a challenging 4,5-branched Kdo trisaccharide was highlighted. The high reactivity of the approach was further demonstrated by the synthesis of a highly crowded 4,5,7,8-branched Kdo pentasaccharide.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Qingyu Yin, Zhiming Li, Fan Wu, Mingtong Ji, Chao Fu, Xiaoyu Wu
Summary: A diastereoselective and enantioselective conjugate addition of alpha-substituted acyl imidazole to nitroalkene catalyzed by nickel bisoxazoline complex and B(C6F5)(3) has been developed. The reaction showed broad substrate tolerance and high yields and enantioselectivity. The coordination catalyst and co-catalyst played a crucial role in the success of the reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Anastasiia Klochkova, Andrey Bubyrev, Dmitry Dar'in, Olga Bakulina, Mikhail Krasavin, Viktor Sokolov
Summary: A novel tandem approach has been developed for the synthesis of various isothiazolidine 1,1-dioxides. The method involves N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition, leading to high yields and trans-diastereoselectivity. The reactivity dependency on the electronic properties of substrates has been investigated.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Analytical
Subbiah Ramesh, Sudalaiyandi Kumaresan
Summary: By developing a coumarin-based naked-eye colorimetric sensor, selective detection of CN- has been achieved in pure aqueous solution with a color change indication. Based on absorption and emission spectral studies, the lowest detection limit of cyanide ion can be estimated accurately.
MICROCHEMICAL JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Zhibing Weng, Ying Zhou, Xin Yue, Feng Jiang, Wengang Guo
Summary: In this study, catalytic asymmetric alpha-regioselective Michael additions of vinylogous alpha-ketoester enolates were conducted efficiently using a chiral bifunctional organocatalyst. The reactions yielded Rauhut-Currier type products with high yields and excellent regio- and enantioselectivities.
Article
Environmental Sciences
Raghavendran Sivasubramanian, Guang-hao Chen, Hamish Robert Mackey
Summary: The addition of divalent cations can greatly benefit high salinity activated sludge systems by improving sludge structure, settling, and organic removal. Lower M/D ratio was found to increase biomass concentrations and reduce extracellular polysaccharides, which are strongly correlated with various shape and surface charge measures. Specific monovalent and divalent cations also play a role in influencing treatment performance and sludge characteristics in high salinity conditions.
Article
Chemistry, Organic
Javed, Ashwani Tiwari, Zanjila Azeem, Pintu Kumar Mandal
Summary: This research reports the potential of the 4,5-dioxo-imidazolinium cation activation strategy for dehydrative glycosylation reactions using geminal dichloroimidazolidinediones (DCIDs) as promoters. The glycosylation between 2-deoxy- and 2,6-dideoxy-sugar hemiacetals with various acceptors was achieved with good yields and high alpha-selectivity. This study not only provides a mild and efficient alternative approach for stereoselective dehydrative glycosylation, but also introduces dichloroimidazolidinedione as a novel promoter in the field of glycoscience.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Daniel Kamzol, Maxime Neuville, Chloe Cocaud, Killian Tiger, Baptiste Taffoureau, Krzysztof Lewinski, Justyna Jaszczyk, Olivier R. Martin, Sebastian Bas, Sylvain Routier, Isabelle Gillaizeau, Frederic Buron, Cyril Nicolas
Summary: This study comprehensively investigates the preparation and reactivity of N-tert-butanesulfinyl glycosylamines with simple Grignard and organo lithium reagents in batch and continuous flow chemistry. These carbohydrate derivatives, acting as latent imine equivalents, react readily with various carbon nucleophiles, making them useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides. Additionally, a hybrid protocol combining flow addition of benzylmagnesium chloride to a (S-R)-arabinofuranosylamine substrate at room temperature with a batch cyclization protocol is introduced for the first time. Notably, this semi-continuous flow process shortens the synthesis of imino-C-glycoside scaffolds to a single workday.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jinhu Wei, Jie-Sheng Huang, Chi-Ming Che
Summary: The chiral Fe-II(N4) complex developed is an effective chiral Lewis acid for the asymmetric conjugate addition of silyl enol ethers to alpha,beta-unsaturated 2-acyl imidazoles, resulting in high yields and enantioselectivities (up to 99% ee) of chiral 1,5-dicarbonyl synthons and cyclohexenone derivatives.
Article
Chemistry, Organic
Qian Chen, Xuanming Zheng, Fang Guo, Kun Liang, Fanrui Zhou
Summary: The study describes a new transition-metal free method for efficiently obtaining alpha-Aminophosphonate analogues containing a phthalazine skeleton under mild conditions. Mechanistic studies using isotope labeling and radical inhibition experiments showed that the transformation involves a nucleophilic addition of dialkyl phosphates rather than an insertion of P-H to carbenes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Lucas L. Baldassari, Anderson C. Mantovani, Samuel Senoner, Boris Maryasin, Nuno Maulide, Diogo S. Ludtke
Article
Chemistry, Multidisciplinary
Debora Muller Pimentel Aroche, Jaqueline Pinto Vargas, Pablo Andrei Nogara, Fabiano da Silveira Santos, Joao Batista Teixeira da Rocha, Diogo Seibert Ludtke, Fabiano Severo Rodembusch
Article
Chemistry, Physical
Eduarda S. Gil, Claudia B. da Silva, Pablo A. Nogara, Carolina H. da Silveira, Joao B. T. da Rocha, Bernardo A. Iglesias, Diogo S. Ludtke, Paulo F. B. Goncalves, Fabiano S. Rodembusch
JOURNAL OF MOLECULAR LIQUIDS
(2020)
Article
Chemistry, Organic
Micaela Jardim, Lucas L. Baldassari, Maria Eduarda Contreira, Angelica Moro, Diogo S. Ludtke
Article
Chemistry, Physical
Natali P. Debia, Juan J. P. Rodriguez, Carolina H. da Silveira, Otavio A. Chaves, Bernardo A. Iglesias, Fabiano S. Rodembusch, Diogo S. Ludtke
JOURNAL OF MOLECULAR LIQUIDS
(2020)
Article
Engineering, Environmental
Raquel Wielens Becker, Marcelo Luis Wilde, Debora Salmoria Araujo, Diogo Seibert Ludtke, Carla Sirtori
Article
Chemistry, Organic
Luana Silva, Alisson R. Rosario, Bianca M. Machado, Diogo S. Ludtke
Summary: This study reported a one-pot procedure for glycosyl amides synthesis using selenocarboxylate as a traceless reagent, and further demonstrated the application of the selenocarboxylate-azide reaction for amide bond formation on a broader range of substrates.
Review
Chemistry, Multidisciplinary
Lucas L. Baldassari, Diogo S. Ludtke
Summary: Selenoesters are important compounds for synthetic purposes due to their ability to participate in various chemical transformations, particularly in the formation of acyl radicals. Scientists have developed multiple methods for synthesizing these compounds from different starting materials.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Environmental Sciences
Pedro Sanabria, Davi Scunderlick, Marcelo L. Wilde, Diogo S. Ludtke, Carla Sirtori
Summary: The study investigated the use of the solar photo-Fenton (SPF) process for the degradation of the breast cancer drug Anastrozole (ANZ), finding high removal rates under specific conditions. Analysis identified different transformation products formed in different matrices, with degradation pathways mainly involving demethylation and hydroxylation.
SCIENCE OF THE TOTAL ENVIRONMENT
(2021)
Article
Engineering, Environmental
Elisabeth Cuervo Lumbaque, Diogo S. Ludtke, Dionysios D. Dionysiou, Vitor J. P. Vilar, Carla Sirtori
Summary: A tube-in-tube membrane photoreactor was proposed to enhance the efficiency of peroxydisulfate treatment, using UV-C radiation and TiO2P25 processes. Tests were conducted to analyze the removal of pharmaceuticals and identify transformation products, suggesting potential pathways of hydroxylation and other reactions.
Article
Chemistry, Multidisciplinary
Lucas L. Baldassari, Anderson C. Mantovani, Micaela Jardim, Boris Maryasin, Diogo S. Ludtke
Summary: A new method for preparing alpha-selanyl-alpha, beta-unsaturated thioesters from propargylthioalkynes and an electrophilic selenium species has been reported. The key lies in the intermediacy of a sulfur-stabilized vinyl cation, which allows for the preparation of 37 examples of the target compounds in good yields. Computational studies have provided insight into the nature of intermediates involved in this transformation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Lucas L. Baldassari, Kelvin S. Santos, Camila P. Ebersol, Diogo S. Ludtke, Angelica Moro
CATALYSIS SCIENCE & TECHNOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Rodrigo S. Fuscaldo, Eduam O. Boeira, Rafael Stieler, Diogo S. Ludtke, Jose R. Gregorio
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2020)
Article
Biochemistry & Molecular Biology
Joao Paulo Bizarro Lopes, Luana Silva, Marco Antonio Ceschi, Diogo Seibert Ludtke, Aline Rigon Zimmer, Thais Carine Ruaro, Rafael Ferreira Dantas, Cristiane Martins Cardoso de Salles, Floriano Paes Silva-Jr, Mario Roberto Senger, Gisele Barbosa, Lidia Moreira Lima, Isabella Alvim Guedes, Laurent Emmanuel Dardenne
Article
Chemistry, Organic
Andressa M. M. Carlos, Rafael Stieler, Diogo S. Ludtke
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
