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Aziridines, structurally related to epoxides, are among the most challenging and fascinating heterocycles in organic chemistry due to their increasing applications in asymmetric synthesis, medicinal chemistry, and materials science. These three-membered nitrogen-containing rings serve as key intermediates in the synthesis of chiral amines, complex molecules, and pharmaceutically relevant compounds. This review provides an overview of recent progress in catalytic asymmetric aziridination, focusing on novel methodologies, an analysis of the scope and limitations of each approach, and mechanistic insights.
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http://dx.doi.org/10.1007/s41061-025-00519-7 | DOI Listing |
ACS Electrochem
September 2025
Department of Material Science and Engineering, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
Bipolar membranes (BPMs) are increasingly recognized as a promising electrolyte option for water electrolysis, attributable to their distinctive properties derived from the membrane's layered structure, which consists of an anion exchange (AEL) and a cation exchange layer (CEL). This study investigates four different BPMs and the influence they have on the performance of a water electrolysis cell under two different feed configurations: (1) a symmetric deionized water feed to both anode and cathode compartments and (2) an asymmetric feed with a 0.5 mol/L NaCl catholyte feed and a deionized water anolyte feed.
View Article and Find Full Text PDFBeilstein J Org Chem
August 2025
College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, China.
Beyond the conventional carbon-centered chirality, catalytic asymmetric transformations of isocyanides have recently emerged as a powerful strategy for the efficient synthesis of structurally diverse scaffolds featuring axial, planar, helical, and inherent chirality. Herein, we summarize the exciting achievements in this rapidly evolving field. These elegant examples have been organized and presented based on the reaction type as well as the resulting chirality form.
View Article and Find Full Text PDFOrg Biomol Chem
September 2025
School of Chemistry & Environment; Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Yuehua Street, Kun-ming 650504, China.
The present study utilizes density functional theory (DFT) to systematically investigate the effect of a ligand on the mechanism of nickel-catalyzed asymmetric hydrogenation of cyclic -sulfonyl imines, employing alcohol protons as the hydrogen source. By comparing the free energies of three catalytic pathways involving various coordinated nickel complexes with different ligands, we identify that the enantio-determining step is the nickel-hydride transfer. Notably, the reaction pathway initiated by the Ni(0) species through oxidative addition of alcohol is determined to be the most favorable.
View Article and Find Full Text PDFOrg Biomol Chem
September 2025
Department of Chemistry & Biochemistry, North Dakota State University, Fargo-58102, USA.
The Mukaiyama-Michael (M-M) reaction is a powerful approach for carbon-carbon bond formation and can provide access to all-carbon quaternary centers and vicinal stereocenters. The use of chiral catalysts for this transformation has enabled the development of efficient asymmetric methods in which the reaction proceeds with high enantioselectivity in the presence of only a substoichiometric amount of the chiral promoter. Both chiral Lewis acid catalysts and organocatalysts have been employed.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
By the strategic integration of squaramide with amino acid derivatives, a type of modular H-bonding catalyst for the enantioselective hydrogen atom transfer (HAT) process was developed. With these disulfides, a photoinduced asymmetric anti-Markovnikov hydrophosphinylation was achieved, providing a series of chiral -hydroxyphosphine oxides with reasonable to high enantioselectivity. Mechanism studies revealed the critical role of the H-bonding interactions between the squaramide scaffold and radical intermediates in governing the enantioselectivity and catalytic reactivity.
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