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In this protocol, an efficient palladium-catalyzed asymmetric synthesis of axially chiral conjugated dienes via alkenyl C-H olefination is reported. The corresponding atropisomeric styrenes containing a conjugated diene scaffold were obtained in good yields with good enantioselectivities. This synthetic strategy features an easy operation, mild reaction conditions, a wide functionality tolerance, and high efficiency.
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http://dx.doi.org/10.1021/acs.orglett.2c00386 | DOI Listing |
Beilstein 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 PDFChemistry
September 2025
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, 9808578, Japan.
Phosphorus(V)-centered porphyrins (P(V)-porphyrins) are an important class of functional dyes in many fields of research, and axial ligands on the phosphorus atom affect the electronic properties of P(V)-porphyrins and add functions. Herein, we report on the synthesis and characterization of a hitherto unknown P(V)-porphyrin having hydrogen atoms as axial ligands (1·PF , PF is a counter anion). Synthesis of 1·PF was achieved by treatment of dichloro-derivative (2·Cl) with LiAlH followed by AgPF via hydride reduction accompanied by one-electron reduction and one-electron oxidation.
View Article and Find Full Text PDFOrg Lett
September 2025
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610093, P. R. China.
The first enantioselective Bora-Brook rearrangement reaction catalyzed by a Cu/SOP system was established. In this protocol, the synthesis of axially chiral monoaldehydes has been achieved by the desymmetric reduction of prochiral dialdehydes. This reaction proceeds smoothly under mild conditions, affording the products in high yields (up to 91%) with excellent enantioselectivities (up to 96:4 er) while exhibiting broad functional group compatibility.
View Article and Find Full Text PDFOrg Lett
September 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Herein, we report the first total synthesis of the conjugation-ready tetrasaccharide repeating unit of the O-antigen from NCTC 8505. This work features a novel synthetic route for the incorporation of the α-linked l-galactosaminuronic acid (l-GalpNAcA) moiety in oligosaccharide synthesis. The target molecule poses several challenging elements, including synthesis of rare sugar units, such as d-bacillosamine and l-GalpNAcA, inherently poor nucleophilicity of the axial 4-hydroxyl group of l-galactosamine, and its demanding stereoselective couplings.
View Article and Find Full Text PDFFront Cell Infect Microbiol
September 2025
Department of General Surgery, Affiliated Zhongshan Hospital of Dalian University, Dalian, Liaoning, China.
The rising prevalence of multidrug-resistant (MDR) foodborne pathogens, particularly spp., necessitates alternative antimicrobial solutions. Phage therapy offers a promising solution against MDR Gram-negative infections; however, its clinical application is constrained by the presence of endotoxins, residual cellular debris, the risk of horizontal gene transfer by temperate phages, and an incomplete understanding of how phage structural integrity influences infectivity and enzyme function.
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