ChemPlusChem, Год журнала: 2023, Номер 88(10)
Опубликована: Авг. 7, 2023
By combining tandem asymmetric gold catalysis and subsequent stereoconvergent hydrolysis of enol ester in a one-pot process, hydroxylated propargylic esters are converted into chiral β-oxygenated ketones with mostly good enantiomeric ratios largely to excellent yields. The product center is formed via stereoselective cyclization allenyl intermediate, which enabled by gold-ligand cooperation.
Язык: Английский
Organic Letters, Год журнала: 2024, Номер 26(15), С. 3037 - 3042
Опубликована: Апрель 1, 2024
A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl octahydro-2,4-methanoazulen-1-yl esters that relies on gold(I)- chiral Brønsted acid-catalyzed cycloisomerization/Diels–Alder (CDA) reaction (E)-1,10-dien-4-yn-3-yl acetates is described.
Язык: Английский
Процитировано
2
Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(3), С. 761 - 768
Опубликована: Ноя. 27, 2023
A method to prepare a structurally diverse range of spirocyclic cyclopentanes, furans, pyrrolidines and piperidines, which relies on the gold( i )-catalyzed spirocyclization 1-ene-4,9- 3-ene-1,7-diyne esters, has been developed.
Язык: Английский
Процитировано
6
ACS Catalysis, Год журнала: 2023, Номер 14(1), С. 574 - 584
Опубликована: Дек. 26, 2023
Controlling the reaction selectivity to realize divergent syntheses is a permanent pursuit for chemists. Reported herein chemodivergent palladium-catalyzed method that enables synthesis of structurally valuable internal alkynes and/or terminal 1,3-dienes from readily available propargylic carbonates through carbonyl umpolung. In presence Pd catalyst/P-ligand, propargyl alkylation complements traditional coupling nonstabilized nucleophiles with electrophiles by employing carbonyls as source umpolung alkyl carbanions and surrogates organometallic reagents. dienylation chemistry, use Pd–NHC combination regulated product distribution, thus providing catalytic alternative otherwise inaccessible branched sequence allenylation skeletal isomerization in chemoselective regioselective manner. Additionally, versatile products can be transformed resulting 1,3-dienes, further highlighting broad synthetic potential these discoveries.
Язык: Английский
Процитировано
5
Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(14)
Опубликована: Май 8, 2024
A novel gold (I)-catalyzed synthetic strategy has been achieved for an efficient construction of indenylidene derivatives from substituted 1,6-diynes. This reaction describes the unique reactivity catalysis in facilitating intramolecular [3,3]-sigmatropic rearrangement, 5-exo dig cyclization followed by 1,5-migration acryl group, resulting formation indenylidenes. Various indenylidenes were successfully synthesized with up to 92 % yields. In this protocol, two new C-C bonds sequentially formed atom economically one pot.
Язык: Английский
Процитировано
1
Chemical Science, Год журнала: 2024, Номер 15(24), С. 9361 - 9368
Опубликована: Янв. 1, 2024
The stereoselective construction of furan/pyrrole-fused eight-membered heterocycles via chiral gold-catalyzed (4 + 4) cycloadditions was realized.
Язык: Английский
Процитировано
1
Organic Letters, Год журнала: 2024, Номер 26(31), С. 6675 - 6680
Опубликована: Июль 25, 2024
A novel, highly stereoselective gold-catalyzed spirocyclization of 2-benzyl-3-alkynyl chromone with nitrone is described. This cascade reaction involves cycloisomerization, nitrone-olefin [3 + 2]-annulation, alkene oxidation, and rearrangement for the formation spirocyclic products. Interestingly, isoxazolidine ring generated from 2]-annulation donates oxygen to generate a new pyran-3(4
Язык: Английский
Процитировано
1
Israel Journal of Chemistry, Год журнала: 2023, Номер 63(9)
Опубликована: Авг. 10, 2023
Abstract A one‐pot synthesis of 2‐acylidene‐3‐oxindole and azaaurone derivatives starting from O ‐alkynylanilines alkynes is presented. By means oxidative gold catalysis the two materials are transferred to reactive intermediates that in situ form target products. This double oxidation strategy enables a protecting group‐free step‐economic towards these valuable substrate classes.
Язык: Английский
Процитировано
2
Organic Letters, Год журнала: 2024, Номер 26(36), С. 7713 - 7717
Опубликована: Авг. 29, 2024
Sulfenylated propargylic carboxylates were introduced to investigate the influence of sulfur substitution in gold-catalyzed alkyne activation pathways. Regiodivergent rearrangement and indole capture reactions proceed under mild conditions give functionalized products bearing sulfenylated (
Язык: Английский
Процитировано
0
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(16), С. 4371 - 4379
Опубликована: Янв. 1, 2024
DFT calculations proposed a new mechanism for the formation of bridged ring and elucidated solvent-controlled chemodivergence reaction, with involvement key allyl-gold species.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2024, Номер 26(27), С. 5817 - 5821
Опубликована: Июль 1, 2024
Enantioconvergent transformations from racemic mixtures are attractive since they allow to generate optically active products with full conversion despite the possibly adverse kinetic resolution process.When dealing gold(I)-catalyzed cycloisomerizations, chirality transfer precursor is another possible diverting pathway, which renders enantioconvergence challenging.Not surprisingly, enantioconvergent Au(I)-catalyzed processes have remained extremely rare.Herein, we show that cavity-driven catalysis using β-Cyclodextrin-NHC-Au(I) complexes bring opportunities conduct highly cycloisomerizations of 1,5-enynes, -enynols and -enynyl esters.
Язык: Английский
Процитировано
0