Article
Chemistry, Inorganic & Nuclear
Guoqi Zhang, Haisu Zeng, Quan Tang, Selin Ates, Shengping Zheng, Michelle C. Neary
Summary: A study on the regioselective epoxide ring-opening through hydroboration catalysed by a vanadium(III) dialkyl complex supported by a redox-active terpyridine ligand is reported. The effective Markovnikov hydroboration of terminal epoxides led to the synthesis of secondary alcohols in high yields, demonstrating a new catalytic application of an earth-abundant vanadium(III) complex.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Niharika Sinha, Anchal Singhal, Deeksha Sharma, Shiv Murat Singh Chauhan
Summary: In this study, the calix[4]pyrrole is introduced as a novel organocatalyst for regioselective ring-opening of epoxides. Vicinal halohydrins can be obtained in good to excellent yields (75-95%) using elemental halogen as a nucleophile. The reactivity of the halide ion is influenced by factors such as solvent polarity, temperature, and non-covalent interactions with the functional group on the calix[4]pyrrole moiety.
LETTERS IN ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Manoj K. Jaiswal, Abhishek Gupta, Mangal S. Yadav, Vinay K. Pandey, Vinod K. Tiwari
Summary: A novel organocatalyzed [3+2] cycloaddition reaction has been developed for the construction of 1,5-disubstituted triazolyl glycoconjugates. The reaction involves the use of Schreiner thiourea organocatalysts to activate nitroolefins through double hydrogen bonding. This metal-free and acid-free synthetic protocol is operationally simple, regioselective, and complements the classical RuAAC catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles. By using catalytic amounts of the Schreiner thiourea organocatalyst, a wide range of organic azides can react with nitroolefins to produce diverse 1,5-disubstituted 1,2,3-triazoles in good yields with excellent regioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Kai-Qiang Tian, Tongbo Zhang, Shi-Jiao Zhang, Jun Zhao, Leilei Mao, Guiyun Duan, Hong-Shuang Li
Summary: This study developed a method for the synthesis of pyrido[1,4]oxazocines from 4-Cl- and 2-Cl-substituted 3-(oxiran-2-yl)pyridines and ethanolamines under additive-free conditions. The method exhibits regioselectivity and efficiency.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Jonali Das, Raju Chouhan, Hemi Borgohain, Biraj Jyoti Borah, Sajal Kumar Das
Summary: The regio- and diastereoselective synthesis of cyclic carbamates is challenging but important. The intramolecular ring-opening cyclization of N-Boc-tethered epoxides has many favorable features but has been underexplored for 1,3-oxazinan-2-ones. Here, we demonstrate that a two-carbon tether connecting the epoxide and N-Boc moieties enables the efficient synthesis of 1,3-oxazinan-2-ones containing vicinal stereocenters.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Fu-Yu Li, Bei Wang, Hong Xu, Yao Xiao, Dong-Wei Huang, Ji-Yu Wang
Summary: A series of synthetically challenging oxazolidinone compounds were successfully synthesized via a regioselective radical addition reaction of azonaphthalenes. The development of an iron-catalyzed reduction radical cascade strategy was carried out for the construction of poly-substituted oxazolidinones, particularly the synthesis of complex spiro oxazolidinones, which was of significant importance. Furthermore, the products could also be transformed into unreported and valuable oxadiazin-2-one and β-hydroxyhydrazine compounds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Antoine d'Aleman, Oscar Gayraud, Catherine Fressigne, Emilie Petit, Laetitia Bailly, Jacques Maddaluno, Michael De Paolis
Summary: The lactonization of 2-(2-nitrophenyl)-1,3-cyclohexanediones containing an alcohol side chain and up to three distant prochiral elements is achieved through isomerization mediated by simple organocatalysts such as quinidine. This reaction produces strained nonalactones and decalactone with up to three stereocenters in high er and dr (up to 99 : 1) through a process of ring expansion. Various distant groups, including alkyl, aryl, carboxylate, and carboxamide moieties, were investigated.
Article
Chemistry, Multidisciplinary
Lucia Veltri, Roberta Amuso, Paola Vitale, Maria A. Chiacchio, Cinzia Benincasa, Bartolo Gabriele
Summary: A new process has been developed for the high value added conversion of carbon dioxide to 1,3-oxazine-2,4-diones through catalytic carboxylative heterocyclization of readily available 3-ynamides, yielding products in 44-85% yields under relatively mild conditions.
JOURNAL OF CO2 UTILIZATION
(2021)
Article
Chemistry, Applied
Yuki Kanai, Dorian Mueller-Borges, Herbert Plenio
Summary: The direct arylation of 1,3-benzodioxole and 2,2-difluorobenzo[1,3]dioxole with various aryl bromides yields 4-substituted products in high yields. The nature of the amide and the concentration of the reactants play crucial roles in optimizing reaction conditions. Acetamide acts as a ligand to Pd, not as a solvent, in this reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Yi-Xuan Ding, Zhou-Hao Zhu, Han Wang, Chang-Bin Yu, Yong-Gui Zhou
Summary: A Ru-catalyzed hydrogenative desymmetrization was developed for constructing three stereocenters in a compound, including two coherent and discontiguous chiral centers and a chiral quaternary carbon, with excellent enantio- and diastereoselectivities. Stereodivergent synthesis of four stereoisomers could be conducted with high enantios-electivities, and the reaction could be achieved at gram scale without loss of reactivity and optical purity, resulting in a completed formal synthesis of the bioactive molecule (-)-isocelorbicol.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Organic
Qing-Qiang Su, Ruo-Nan Wang, Yong-Zheng Lv, Ya-Xin Fan, Shan Li, Hong-Li Huang, Ji-Yuan Du
Summary: This study presents a one-pot cycloaddition reaction of ethynyl indoloxazolidones with 1,3-cyclohexanediones enabled by copper catalysis, leading to a series of functionalized furan derivatives in good yields. The method demonstrates mild reaction conditions, high efficiency, and wide substrate scope.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Polymer Science
Danielle D. Harrier, Damien Guironnet
Summary: By utilizing a droplet microfluidic encapsulation strategy, we have successfully synthesized dispersed polyester and polyether particles in water. Through adjusting the viscosity, surface tension, and hydrophobicity of the droplets, we enhanced the stability of the catalyst, resulting in higher monomer conversion and higher molecular weight polymer.
Article
Chemistry, Organic
Feng Jiang, Tengfei Meng, Ying Zhou, Zhenying Xiong, Yupei Zhao, Wengang Guo
Summary: We report an enantio- and diastereodivergent synthesis of enantioenriched fluorenes with broad substrate scope and high enantioselectivity (up to 99% ee) under low catalyst loading (0.1 mol %). The success of this method lies in the pseudo-diastereodivergent desymmetrization of stereoisomers of meso-epoxides enabled by the same organocatalyst. Furthermore, some of the chiral fluorenes obtained exhibit high fluorescence quantum yields (up to 76.6%), as evidenced by photophysical properties studies.
Article
Chemistry, Organic
Shengsheng Qiang, Rong-Bin Hu, Ying-Yeung Yeung
Summary: Herein, an efficient zwitterion-catalyzed epoxide ring-opening with carboxylic acids is reported, providing a convenient method for the synthesis of 1,2-diol monoesters. The catalytic protocol shows a broad substrate scope and also allows the use of aziridine as a substitute for epoxide. The zwitterionic catalyst can be easily recycled by aqueous extraction, demonstrating the synthetic utilities of the 1,2-diol monoesters.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Na Shao, Valerie Monnier, Laurence Charles, Jean Rodriguez, Cyril Bressy, Adrien Quintard
Summary: This study reports a multicatalytic strategy for the synthesis of a new type of scaffold containing a tetrasubstituted stereocenter embedded in fluorohydrin motifs. The method involves organocatalyzed fluorination and diastereoselective aldol reaction, resulting in the stereoselective synthesis of fluorinated 1,3-diols.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
