The Journal of Physical Chemistry A, Journal Year: 2024, Volume and Issue: 128(32), P. 6729 - 6738
Published: Aug. 7, 2024
This study elucidates the mechanisms and principles governing chemoselectivity in synthesizing two distinct N-heterocycles, benzimidazole thiazine benzothiazole imidazole, through BF
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(46)
Published: July 25, 2024
Abstract An unprecedented chemodivergent strategy for parallel kinetic resolution (PKR) is disclosed through which two planar chiral products bearing different structures were simultaneously afforded with opposite stereoselectivities. Two achiral esters are activated by one single N‐heterocyclic carbene (NHC) catalyst to react the enantiomers of racemic imine substrate in a fashion. distinct and stereoselectivities respectively from same reaction system good excellent yields, enantio‐ diastereoselectivities. Control experiments studies carried out probe dynamic properties during progress. The pyridine lactam show interesting applications both asymmetric synthesis pesticide development.
Language: Английский
Citations
4
ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3860 - 3872
Published: Feb. 19, 2025
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 18, 2025
We report a chiral phosphoric acid-catalyzed hydrolytic parallel kinetic resolution (HPKR) of racemic epoxides and activated alcohols. Using an acyloxy-assisted activation strategy, this method enables the highly stereocontrolled hydrolysis under mild conditions. A wide range aryl-substituted secondary alcohols were effectively transformed, providing corresponding with combined yields up to 99% enantiomeric ratios exceeding 99:1.
Language: Английский
Citations
0
Chemical Science, Journal Year: 2023, Volume and Issue: 14(43), P. 12152 - 12159
Published: Jan. 1, 2023
An intriguing chiral phosphoric acid-catalyzed asymmetric hydrolytic ring-opening of racemic aziridines via regiodivergent PKR is presented, providing an efficient approach for the construction β-amino alcohols.
Language: Английский
Citations
9
Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6290 - 6294
Published: July 18, 2024
Strategies that fully convert available racemic substrates into valuable enantioenriched products are urgently needed in organic synthesis. Reported herein is the first parallel kinetic asymmetric transformation of cyclohexadienones. Racemic cyclohexadienones diastereoselectively converted a new pair transient dienol intermediates, which then protonated by chiral phosphoric acid to deliver two sets hydroindole bearing quaternary stereocenter with generally excellent enantioselectivity.
Language: Английский
Citations
2
JACS Au, Journal Year: 2024, Volume and Issue: 4(11), P. 4445 - 4454
Published: Oct. 14, 2024
The development of chiroptical molecular switches for chiral sensing, data communication, optical displays, logic gates, and asymmetric catalysis is currently a vibrant frontier science technology. Herein, we report practical artificial dynamic system based on 1,2-diaxial atropisomer. Organocatalytic parallel kinetic resolution allows the divergent synthesis two sets stereoisomers with vicinal C-C N-N axes from same racemic single-axis substrates. By simply varying configuration single catalyst, all four are accessible. successive conduction covalent unlocking/locking thermal-isomerization processes enables sequential switching between atropisomeric states electronic circular dichroism signal reversal, providing an example multistate switches.
Language: Английский
Citations
2
ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18701 - 18707
Published: Dec. 8, 2024
Chiral 2,5-disubstituted pyrrolidines are ubiquitous subunits in natural products, bioactive compounds, pharmaceuticals, and chiral catalysts. However, their asymmetric synthesis still presents a formidable challenge. We herein report rare example of diastereodivergent parallel kinetic resolution racemic 2-substituted via C(sp3)–H borylation. A vast array enantioenriched cis- trans-2,5-disubstituted were obtained with high enantioselectivities. The synthetic utility was demonstrated by downstream transformations, including the optically active pyrrolidine 197B cis-pyrrolidine 225H.
Language: Английский
Citations
1
Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 20, 2024
Comprehensive Summary Herein, a [1,2]‐phospha‐Brook rearrangement‐initiated palladium‐catalyzed cyclization reaction for base‐controlled selective synthesis of 2 H ‐isoindole‐1‐carboxamide and ‐isoindole‐1‐carbonitrile derivatives has been described. This strategy features double isocyanide insertion, efficient bond combinations, simple operation conditions. Mechanistic studies show that the rearrangement is key step in this reaction. protocol offers novel concise ‐isoindole derivatives.
Language: Английский
Citations
1
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4294 - 4322
Published: Aug. 17, 2024
Abstract Optically active molecule architectures stand as an important class of organic compounds and occupy a key role in academic industrial communities. Particularly, the molecules bearing quaternary carbon are vital importance because its favorable conformation valuable three‐dimensional molecules, which frequently play broad spectrum functional materials, pharmaceutical relevant natural agrochemicals. Over past few decades, large number synthetic strategies for enantioselective construction with chiral centers have been focus research initiatives. In this review, state‐of‐the‐art toward synthesis enantioenriched stereocenters summarized, could be segmented into four categories: 1) Construction optically by addition to prochiral sp 2 carbon; 2) all‐carbon via substitution at non‐chiral tetra‐substituted 3) kinetic resolution; 4) desymmetrization reactions.
Language: Английский
Citations
1
ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 201 - 210
Published: Dec. 16, 2024
On the basis of density functional theory (DFT) calculations, we designed an asymmetric synthesis method for axially chiral biaryls through C(sp2)–H imidoylative cyclization isocyanides. Building on this, successfully synthesized compounds containing indole-fused N-heteroaromatic frameworks via palladium-catalyzed C–H imidoylation to achieve high yields and enantioselectivity. Various efficient pathways facilitated ring derivatives with either C–C or C–N axial chirality. This not only provides diverse strategy but also demonstrates that DFT-assisted design is a reliable tool accurately predicting reaction stereoselectivity effectively reducing workload chemical experiments.
Language: Английский
Citations
1