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Unlocking Chiral Sulfinimidoyl Electrophiles: Asymmetric Synthesis of Sulfinamides Catalyzed by Anionic Stereogenic-at-Cobalt(III) Complexes.
J Am Chem Soc
January 2025
Department of Applied Chemistry, Anhui Province Engineering Laboratory for Green Pesticide Development and Application, and Anhui Province Key Laboratory of Crop Integrated Pest Management, Anhui Agricultural University, Hefei 230036, China.
Asymmetric catalysis involving a sulfoxide electrophile intermediate presents an efficient methodology for accessing stereogenic-at-sulfur compounds, such as sulfinate esters, sulfinamides, , which have garnered increasing attention in modern pharmaceutical sciences. However, as the aza-analog of sulfoxide electrophiles, the asymmetric issues about electrophilic sulfinimidoyl species remain largely unexplored and represent a significant challenge in sulfur stereochemistry. Herein, we exhibit an anionic stereogenic-at-cobalt(III) complex-catalyzed asymmetric synthesis of chiral sulfinamides via chiral sulfinimidoyl iodide intermediates.
View Article and Find Full Text PDFConformational Chirality of Single-Crystal Covalent Organic Frameworks.
J Am Chem Soc
December 2024
College of Chemistry and Molecular Engineering, Beijing National Laboratory for Molecular Sciences, Peking University, Beijing 100871, China.
The crystallization of organic polymers is often hindered by chiral units, hence resulting in chiral organic polymers typically existing as amorphous or partially crystalline phases such as natural rubber and cellulose. Similarly, as an emerging crystalline chiral polymer, chiral covalent organic frameworks (COFs) also inevitably face a delicate balance between chiral units and crystallization, limiting their production and applications in separation, catalysis, and optics. Here, we present a general strategy for producing a series of conformational chiral COFs with high crystallinity through breaking the meso conformation of achiral COFs.
View Article and Find Full Text PDFEnantioselective Cascade Catalysis for the Construction of Tetrahydroquinolines.
Org Lett
November 2024
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, People's Republic of China.
Secondary amines are widely used as robust catalysts for the enantioselective functionalization of aldehydes, yet they are rarely employed as Lewis bases or hydrogen-bonding catalysts for alkene activation. In this study, we present a decarboxylative [4 + 2] cycloaddition of vinyl benzoxazinanones with nitroolefins to construct tetrahydroquinolines through cascade catalysis. A single chiral morpholine catalyst sequentially functions as both a Lewis base and a hydrogen-bonding catalyst.
View Article and Find Full Text PDFComputational design for enantioselective CO capture: asymmetric frustrated Lewis pairs in epoxide transformations.
Beilstein J Org Chem
October 2024
Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
Carbon capture and utilisation (CCU) technologies offer a compelling strategy to mitigate rising atmospheric carbon dioxide levels. Despite extensive research on the CO insertion into epoxides to form cyclic carbonates, the stereochemical implications of this reaction have been largely overlooked, despite the prevalence of racemic epoxide solutions. This study introduces an in silico approach to design asymmetric frustrated Lewis pairs (FLPs) aimed at controlling reaction stereochemistry.
View Article and Find Full Text PDFStereochemical Impacts on Acyclic Mechanochemical Carbon-Carbon Bond Activation.
Angew Chem Int Ed Engl
October 2024
Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis, Technion - Israel Institute of Technology, Haifa, 3200008, Israel.
The influence of stereochemistry on the mechanochemistry rate is studied using a new mechanophore based on a benzopinacol (BP) skeleton. Two sets of BP diastereomers, the meso R,S and the R,R/S,S were isolated, incorporated into the center of a poly(methyl acrylate), and their mechanical activation rate was measured in solution. Under mechanical stress, the central C-C bond in BP is cleaved, providing two independent benzophenone molecules with higher UV-absorption coefficient at 254 nm.
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