Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(3), P. 100918 - 100918
Published: Feb. 7, 2024
Language: Английский
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(9), P. 5439 - 5446
Published: Feb. 22, 2023
Direct construction of chiral S(VI) from prochiral S(II) is a formidable challenge due to the inevitable formation stable S(IV). Previous synthetic strategies rely on conversion S(IV) or enantioselective desymmetrization preformed symmetrical substrates. Here, we report desymmetrizing hydrolysis in situ-generated symmetric aza-dichlorosulfonium sulfenamides for preparation sulfonimidoyl chlorides, which could be used as general synthon obtaining series derivatives.
Language: Английский
Citations
60
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(14)
Published: Feb. 10, 2023
Axially chiral diaryl ethers are a type of unique atropisomers bearing two potential axes, which have applications in variety research fields. However, the catalytic enantioselective synthesis these ether is largely underexplored when compared to asymmetric biaryl or other types atropisomers. Herein, we report highly efficient through an organocatalyzed desymmetrization protocol. The phosphoric acid-catalyzed electrophilic aromatic aminations symmetrical 1,3-benzenediamine substrates afforded series excellent yields and enantioselectivities. facile construction heterocycles by utilizations 1,2-benzenediamine moiety products provided access structurally diverse novel azaarene-containing
Language: Английский
Citations
48
Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(4), P. 692 - 710
Published: March 3, 2021
Abstract Kinetic resolution, dynamic kinetic resolution and desymmetrization are practical methods to produce enantioenriched products from relatively simple racemic or achiral starting materials, which also sometimes difficult be accessed by other asymmetric methods. Chiral phosphoric acids, have been recognized as one of the most powerful chiral organocatalysts date, extensively applied in above‐mentioned research fields. In this minireview, we summarized tremendous development reactions enabled acids since year 2016, were not included two previous outstanding reviews Petersen et al Dixon al. A number examples involving use CPA cooperative catalyst review.
Language: Английский
Citations
77
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(10)
Published: Jan. 10, 2022
Chiral hydrogen-bonding (H-bonding) catalytic asymmetric conjugate addition to activated olefins has been widely used access enantioenriched molecules containing stereocenters at the β-position of olefin activating groups. Herein, we report first highly enantioselective radical-based manifold. Under a dual organocatalyst system involving chiral phosphoric acid and DPZ as photoredox sensitizer, transformations N-arylglycines, in which aryls with CF3 substituents are introduced, alkenyl azaarenes afforded valuable hydroaminoalkylation adducts satisfactory results. In diversity azaarenes, method can be construct aryl-, alkyl- silyl-substituted stereocenter. Control experiments density functional theory calculations were performed elucidate plausible reaction mechanism origin stereoselectivity, wherein nonclassical H-bonding interactions found assist catalysts offering sufficient enantiocontrol.
Language: Английский
Citations
62
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(22)
Published: March 16, 2022
An efficient approach for asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been disclosed through enantioselective electrophilic aromatic aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. A wide range bearing varied ring sizes (16 to 23-membered) and functional group-containing ansa chains were readily afforded using this method, excellent yields high enantioselectivities (23 examples, up 99.5 : 0.5 er). Experimental studies DFT calculations performed elucidate the mechanism origin stereoselectivities these reactions. Preliminary utilization macrocycle as organocatalyst showcased potential applications novel skeletons.
Language: Английский
Citations
46
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(17), P. 3477 - 3502
Published: Jan. 1, 2023
This review article presents an in-depth analysis of the strategies and methodologies for using chiral phosphoric acids as organocatalysts in asymmetric syntheses from recent literature.
Language: Английский
Citations
32
Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(9), P. 1923 - 1957
Published: Jan. 9, 2019
Abstract The broad prospects of trifluoromethylated compounds in materials science, agricultural chemistry, and pharmaceutical chemistry have stimulated the rapid development asymmetric organocatalytic transformations to access these biologically important compounds. Among all types compounds, cyclic with a C−CF 3 stereogenic center gained increasing attention medicinal organic because they are extensively found many active molecules, lead listed drugs. This review attempts summarize developments synthesis bearing since 2012. magnified image
Language: Английский
Citations
73
Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(52), P. 23598 - 23602
Published: Sept. 14, 2020
Abstract A versatile kinetic resolution of protecting‐group‐free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. series mono‐N‐protected unprotected BINAMs, diphenyl diamines NOBIN derivatives could be kinetically resolved excellent performances (with s factor up to 420). The gram‐scale reactions facile derivatizations the products demonstrate potential these methods in asymmetric synthesis catalysts ligands.
Language: Английский
Citations
70
Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(6), P. 2333 - 2337
Published: Dec. 3, 2019
An efficient method for the asymmetric synthesis of 4H-3,1-benzoxazines was developed by kinetic resolution 2-amido benzyl alcohols using chiral phosphoric acid catalyzed intramolecular cyclizations. A broad range (both secondary and tertiary alcohols) were kinetically resolved with high selectivities, an s factor up to 94. Mechanistic studies performed elucidate mechanism these reactions, wherein amide moieties reacted as electrophiles. Gram-scale reaction facile transformations products demonstrate potential this in biologically active heterocycles.
Language: Английский
Citations
60
Chemical Science, Journal Year: 2021, Volume and Issue: 12(44), P. 14920 - 14926
Published: Jan. 1, 2021
The first chiral phosphoric acid (CPA) catalyzed cycloaddition-elimination cascade reaction of 2-naphthol- and phenol-derived enecarbamates with azonaphthalenes has been established, providing a highly atroposelective route to an array axially aryl-C3-benzoindoles in excellent yields enantioselectivities. success this strategy derives from the stepwise process involving CPA-catalyzed asymmetric formal [3 + 2] cycloaddition subsequent central-to-axial chirality conversion by elimination carbamate. In addition, practicality had verified varieties transformations towards functionalized atropisomers.
Language: Английский
Citations
47