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Nickel(II)/Salox-Catalyzed Enantioselective C-H Functionalization.
ACS Cent Sci
January 2025
Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
Recently, nickel catalysts have garnered considerable attention for their efficacy and versatility in asymmetric catalysis, attributed to their distinctive properties. However, the use of cost-effective and sustainable divalent nickel catalysts in C-H activation/asymmetric alkene insertion poses significant challenges due to the intricate control of stereochemistry in the transformation of the tetracoordinate C-Ni(II) intermediate. Herein, we report a Ni(II)-catalyzed enantioselective C-H/N-H annulation with oxabicyclic alkenes.
View Article and Find Full Text PDFAsymmetric Three-Component Radical Cascade Reactions Enabled by Synergistic Photoredox/Brønsted Acid Catalysis: Access to α-Amino Acid Derivatives.
ACS Cent Sci
January 2025
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Multicomponent reactions (MCRs), highly sought-after methods to produce atom-, step-, and energy-economic organic syntheses, have been developed extensively. However, catalytic asymmetric MCRs, especially those involving radical species, remain largely unexplored owing to the difficulty in stereoselectively regulating the extraordinarily high reactivity of open-shell radical species. Herein, we report a conceptually novel catalytic asymmetric three-component radical cascade reaction of readily accessible glycine esters, α-bromo carbonyl compounds and 2-vinylcyclopropyl ketones via synergistic photoredox/Brønsted acid catalysis, in which three sequential C-C (σ/π/σ) bond-forming events occurred through a radical addition/ring-opening/radical-radical coupling protocol, affording an array of valuable enantioenriched unnatural α-amino acid derivatives bearing two contiguous stereogenic centers and an alkene moiety in moderate to good yield with high diastereoselectivity, excellent enantioselectivity and good -dominated geometry under mild reaction conditions.
View Article and Find Full Text PDFA stereochemical model and origins of selectivity for the rhodium-catalyzed hydroselenation of styrene.
Dalton Trans
January 2025
Chongqing Key Laboratory of Green Catalysis Materials and Technology, College of Chemistry, Chongqing Normal University, Chongqing 401331, China.
A deeper understanding of the mechanisms underlying transition metal-catalyzed transformation is crucial for developing innovative strategies to synthesize chiral organoselenium compounds. In this study, we developed and investigated a three-layer chirality relay model for the rhodium-catalyzed asymmetric hydroselenation of alkenes through density functional theory (DFT) calculations. In the back layer of this model, the four bulky substituents on the phosphorus atom of the bidentate chiral MeO-BIPHEP ligand were positioned on axial and equatorial bonds, thereby influencing the configuration of the middle layer.
View Article and Find Full Text PDFAsymmetric Organocatalytic 1,6-Conjugate Addition of Alkynyl 8-Methylenenaphthalen-2(8)-one Formed In Situ: Synergistic Construction of Axial and Central Chirality.
Org Lett
January 2025
Taizhou Research Institute, Southern University of Science and Technology, Taizhou 318014, Zhejiang, China.
Organocatalytic enantioselective formal nucleophilic substitution reactions of α-(2-hydroxynaphthalen-8-yl)propargyl alcohols with 1-(1-indol-3-yl)naphthalen-2-ols have been established for the first time. With the aid of a suitable chiral phosphoric acid, alkynyl 8-methylenenaphthalen-2(8)-one was formed in situ from the corresponding α-(2-hydroxynaphthalen-8-yl)propargyl alcohol, followed by enantioselective 1,6-conjugate additions of 1-(1-indol-3-yl)naphthalen-2-ols to afford a number of enantioenriched (,)-2,3-disubstituted indoles in 50-80% yields with 81-93% ee and (,)-2,3-disubstituted indoles in 18-40% yields with 79-96% ee. Notably, these nucleophilic substitution products were characterized by the presence of functional groups, including indole, naphthol, and alkynyl units, while exhibiting both axial and central chirality.
View Article and Find Full Text PDFMulticomponent Modular Synthesis of Chiral Bicyclic Bridged Compounds via an Alkenylfuran-Based Acylation/Rearrangement/Cyclization Sequence.
Org Lett
January 2025
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
The catalytic asymmetric multicomponent acylation/rearrangement/cyclization of alkenylfurans with acyl oxime esters/arylamines or acyl oxime esters/arylamines/hydroxylamine has been developed. This method employs synergistic photoredox/Brønsted acid catalysis, enabling the efficient and versatile synthesis of multifunctionalized [3.2.
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