Organic Letters, Год журнала: 2023, Номер 25(41), С. 7562 - 7566
Опубликована: Окт. 6, 2023
Stereoselective synthesis of bicyclic cyclopentanones was achieved by sequential Tf2O-catalyzed decarboxylation and intramolecular [3 + 2] cycloaddition reactions cyclic enol carbonates bearing an alkene unit. Four stereogenic centers in the obtained cyclopentanone were stereoselectively constructed. This method could be applied to various fused products moderate-to-good yields.
Язык: Английский
Chemical Communications, Год журнала: 2022, Номер 58(68), С. 9500 - 9503
Опубликована: Янв. 1, 2022
A Lewis acid-mediated decarboxylative 1,2-rearrangement reaction of cyclic carbonates was developed. The selectivity the migration in opposite to that corresponding 1,2-diols under same conditions. This contrasting confirmed a variety substrates.
Язык: Английский
Процитировано
3
ChemCatChem, Год журнала: 2023, Номер 15(19)
Опубликована: Авг. 7, 2023
Abstract The biocatalytic kinetic resolution of cyclic carbonates derived from glycerol is reported. A selection 26 esterases and lipases was tested for the asymmetric hydrolysis model substrate (epichlorohydrin carbonate) in aqueous medium. Among them, Pig Liver Esterase Novozym® 435 showed best selectivity with E =38 49, respectively. Both enzymes were employed conversion 12 derivatives under optimized conditions. halogenated afforded unconverted enantiomer up to >99 : 1 er . Furthermore, successfully recycled 10 times without significant loss activity. Upscaling isolation chiral carbonate also demonstrated. Subsequent this building block allowed direct one‐pot synthesis ( S )‐Guaifenesin, )‐Mephenesin )‐Chlorphenesin 89 % yield 94 6
Язык: Английский
Процитировано
1
Organic Letters, Год журнала: 2024, Номер 26(20), С. 4274 - 4279
Опубликована: Май 10, 2024
A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate 2-cyanoacrylate as partners in the presence Pd(PPh
Язык: Английский
Процитировано
0
ACS Catalysis, Год журнала: 2024, Номер 15(1), С. 255 - 264
Опубликована: Дек. 16, 2024
The catalytic asymmetric synthesis of functionalized C2-quaternary indoline scaffolds has garnered significant attention in organic and drug discovery due to the inherent challenges potential applications. Herein, we present a facile approach utilizing Pd-catalyzed intramolecular decarboxylative amination vinyl benzoxazepinones, leading efficient construction challenging chiral 2-vinyl-2-aryl/alkyl frameworks good yields with high enantioselectivities (>50 examples, up 83% yield 97% ee). Furthermore, these indolines can be readily scaled further modified access complex polycyclic structures. We also synthesized several indoline-based ligands that exhibit promising efficiency as catalysts reactions. Computational studies provided insight into inner-sphere mechanism.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2023, Номер 25(41), С. 7562 - 7566
Опубликована: Окт. 6, 2023
Stereoselective synthesis of bicyclic cyclopentanones was achieved by sequential Tf2O-catalyzed decarboxylation and intramolecular [3 + 2] cycloaddition reactions cyclic enol carbonates bearing an alkene unit. Four stereogenic centers in the obtained cyclopentanone were stereoselectively constructed. This method could be applied to various fused products moderate-to-good yields.
Язык: Английский
Процитировано
0