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Catalytic Enantioselective Synthesis of Monosubstituted [n]Paracyclophane using a Desymmetrization/Kinetic Resolution Sequence.
Chemistry
January 2025
Beijing Normal University, College of Chemistry, Xiejiekou NO.19, 100875, Beijing, CHINA.
Optically pure monosubstituted [n]paracyclophanes are promising candidates for material synthesis, asymmetric catalysis, and drug discovery. Thus far, only a few catalytic asymmetric synthesis processes have been reported for assessing these stained atropisomers. In this study, we describe a highly enantioselective synthesis of monosubstituted [n]paracyclophanes by combining desymmetrization and kinetic resolution.
View Article and Find Full Text PDFMolecular Photoelectrocatalysis for Radical Reactions.
Acc Chem Res
January 2025
State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, and Discipline of Intelligent Instrument and Equipment, Xiamen University, Xiamen 361005, P. R. China.
ConspectusMolecular photoelectrocatalysis, which combines the merits of photocatalysis and organic electrosynthesis, including their green attributes and capacity to offer novel reactivity and selectivity, represents an emerging field in organic chemistry that addresses the growing demands for environmental sustainability and synthetic efficiency. This synergistic approach permits access to a wider range of redox potentials, facilitates redox transformations under gentler electrode potentials, and decreases the use of external harsh redox reagents. Despite these potential advantages, this area did not receive significant attention until 2019, when we and others reported the first examples of modern molecular photoelectrocatalysis.
View Article and Find Full Text PDFUnderstanding and quantifying the impact of solute-solvent van der Waals interactions on the selectivity of asymmetric catalytic transformations.
Chem Sci
December 2024
Department of Chemistry, Biology and Biotechnology, University of Perugia Via Elce di Sotto, 8 06123 Perugia Italy
The majority of enantioselective organocatalytic reactions occur in apolar or weakly polar organic solvents. Nevertheless, the influence of solute-solvent van der Waals forces on the relative kinetics of competitive pathways remains poorly understood. In this study, we provide a first insight into the nature and strength of these interactions at the transition state level using advanced computational tools, shedding light into their influence on the selectivity.
View Article and Find Full Text PDFAlkoxy-Directed Dienamine Catalysis in [4 + 2]-Cycloaddition: Enantioselective Synthesis of Benzo-[3]-ladderanol.
J Am Chem Soc
January 2025
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Despite tremendous progress of dienamine catalysis along with its application in enantioselective synthesis over nearly two decades, certain limitations, especially with respect to the regioselectivity in the dienamine generation step, continue to persist. To overcome these shortcomings of classical dienamine catalysis, we now introduce the concept of alkoxy-directed dienamine catalysis and apply it to the enantioselective arene construction by desymmetrizing -enediones through [4 + 2]-cycloaddition. Catalyzed by a diphenylprolinol silyl ether, this reaction utilizes γ-alkoxy α,β-unsaturated aldehydes as the substrate and proceeds in a highly regioselective fashion through the intermediacy of δ-alkoxy dienamine.
View Article and Find Full Text PDFCatalytic Asymmetric 1,4-Hydrocarbonation of 1,3-Enynes via Photoredox/Cobalt/Chromium Triple Catalysis.
Angew Chem Int Ed Engl
January 2025
Shanghai Jiao Tong University, Chemistry, 800 Dongchuan RD. Minhang District, 200240, Shanghai, CHINA.
A synergistic photoredox/cobalt/chromium triple catalysis system for regioselective, enantioselective, and diastereoselective 1,4-hydrocarbonation of readily available 1,3-enyne precursors was explored, providing a modular synthetic platform for various trisubstituted axially chiral allenes bearing an extra central chirality. The protocol features a broad substrate scope, good functional group tolerance, excellent selectivity, and mild reaction conditions. Furthermore, a possible reaction mechanism is proposed based on numerous control experiments and density functional theory calculations.
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