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Multifunctional Magnetic Chiral HKUST MOF Decorated by Triazine, FeO, and Cu(l-Proline) Complex for Green and Mild Asymmetric Catalysis.
ACS Appl Mater Interfaces
December 2024
Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, 14117-13116 Tehran, Islamic Republic of Iran.
A multifunctional magnetic chiral metal-organic framework (MOF) was developed for asymmetric applications by utilizing strategies of chiralization and multifunctionalization. Cu(l-proline)-Triazine/FeO@SiO-NH was employed as a chiral secondary agent to synthesize a chiral hybrid nanocomposite within a MOF. The use of a chiral secondary agent efficiently induces chirality in an achiral MOF structure that cannot be directly chiralized.
View Article and Find Full Text PDFDesign and application of intramolecular arylogous nitroaldol condensation to access 2-aryl-benzofuran and -indole derivatives and formal synthesis of saprisartan.
RSC Adv
November 2024
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT) Hyderabad 500 007 India
This study presents the design and application of intramolecular arylogous nitroaldol (Henry) condensation. A transition metal-free, base-mediated reaction of -heteroatom-substituted aryl aldehydes/ketones and 2-nitrobenzyl (pseudo)halides has been developed to access a wide range of 2-(2-nitroaryl)benzofuran/2-(2-nitroaryl)indole derivatives in high yields. The reaction appears to proceed through -/-benzylation and intramolecular arylogous nitroaldol condensation.
View Article and Find Full Text PDFSelectivity Control in Nitroaldol (Henry) Reaction by Changing the Basic Anion in a Chiral Copper(II) Complex Based on ()-2-Aminomethylpyrrolidine and 3,5-Di--butylsalicylaldehyde.
Molecules
November 2024
A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, Bld. 1, 119334 Moscow, Russia.
This article is a continuation of our previous research on the catalytic capability of a chiral copper complex based on commercially available ()-2-aminomethylpyrrolidine and 3,5-di--butylsalicylaldehyde with various counter-anions in the asymmetric Henry reaction. Our findings indicate that depending on the type of base used, chiral nitroalcohols with yields up to 98% and values up to 77%, as well as β-nitrostyrenes with yields up to 88%, can be produced. Additionally, it has been found that the outcome of the reaction and the catalytic properties of copper (II) complexes ()- and ()- are influenced by the structure of the aldehyde used.
View Article and Find Full Text PDFInterdependent Dynamic Nitroaldol and Boronic Ester Reactions for Complex Dynamers of Different Topologies.
Chemistry
November 2024
Department of Chemistry, KTH - Royal Institute of Technology, Teknikringen 36, S-10044, Stockholm, Sweden.
Complex dynamic systems displaying interdependency between nitroaldol and boronic ester reactions have been demonstrated. Nitroalkane-1,3-diols, generated by the nitroaldol reaction, were susceptible to ester formation with different boronic acids in aprotic solvents, whereas hydrolysis of the esters occurred in the presence of water. The boronic ester formation led to significant stabilization of the nitroaldol adducts under basic conditions.
View Article and Find Full Text PDFEvaluation of the enantioselectivity of new chiral ligands based on imidazolidin-4-one derivatives.
Beilstein J Org Chem
April 2024
Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic.
The new chiral ligands based on derivatives of imidazolidin-4-one were synthesised and characterised. The catalytic activity and enantioselectivity of their corresponding copper(II) complexes were studied in asymmetric Henry reactions. It was found that the enantioselectivity of these catalysts is overall very high and depends on the relative configuration of the ligand used; configuration of ligand affords the nitroaldols with major enantiomer (up to 97% ee), whereas the application of ligands with -configuration led to nitroaldols with major -enantiomer (up to 96% ee).
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