Green Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
NHC-catalyzed desymmetrization amidation of biaryl dialdehydes has been developed for NH-free axially chiral thiourea. Sequential kinetic resolution enhances the chirality induction strategy, expanding applicable scope.
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(30)
Опубликована: Май 15, 2024
Atropisomers hold significant fascination, not only for their prevalence in natural compounds but also biological importance and wide-ranging applications as chiral materials, ligands, organocatalysts. While biaryl heterobiaryl atropisomers are commonly studied, the enantioselective synthesis of less abundant heteroatom-linked non-biaryl presents a formidable challenge modern organic synthesis. Unlike classical atropisomers, these molecules allow rotation around two bonds, resulting low barriers to enantiomerization through concerted bond rotations. In recent years discovery new configurationally stable rare scaffolds such aryl amines, ethers sulfones well innovative methodologies control configuration have been disclosed literature constitute topic this minireview.
Язык: Английский
Процитировано
10
Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 55 - 121
Опубликована: Янв. 9, 2025
Axial chirality is present in a variety of naturally occurring compounds, and becoming increasingly relevant also medicine. Many axially chiral compounds are important as catalysts asymmetric catalysis or have chiroptical properties. This review overviews recent progress the synthesis via organocatalysis. Atroposelective organocatalytic reactions discussed according to dominant catalyst activation mode. For covalent organocatalysis, typical enamine iminium modes presented, followed by N -heterocyclic carbene-catalyzed reactions. The bulk devoted non-covalent activation, where Brønsted acids feature most prolific catalytic structure. last part article discusses hydrogen-bond-donating other motifs such phase-transfer catalysts.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7630 - 7643
Опубликована: Май 13, 2024
Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed ethers via atroposelective esterification dialdehyde-containing ethers. NHC desymmetrization produces ether atropisomers with high yields and enantioselectivities moderate circumstances. Chiral compounds may precursors for highly functionalized bioactivity ligands catalysis.
Язык: Английский
Процитировано
9
Chemical Society Reviews, Год журнала: 2024, Номер unknown
Опубликована: Дек. 18, 2024
This tutorial review provides an overview of various important structural features and reactivity modes NHCs delves deep into the recent advances in NHC-organocatalysis.
Язык: Английский
Процитировано
7
ACS Catalysis, Год журнала: 2024, Номер 14(9), С. 6667 - 6673
Опубликована: Апрель 16, 2024
C–O axially chiral diaryl ethers play important roles in natural products and bioactive molecules, but because of the low rotational barrier strict steric hindrance requirements, catalytic asymmetric construction still remains a challenge. Herein, we devised strategy employing achiral azlactone for desymmetrization prochiral diamines under catalysis phosphoric acid. The targeted were obtained very good yields (up to 98%) high enantioselectivities >99.5:0.5 er). synthetic utility was demonstrated through large-scale reaction transformations products. Moreover, DFT calculations conducted probe origins enantioselectivity.
Язык: Английский
Процитировано
6
European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(28)
Опубликована: Май 16, 2024
Abstract Axially chiral biaryl scaffolds are important in pharmaceuticals, natural products, and asymmetric synthesis. Atroposelective ring‐opening of configurationally labile reagents via dynamic kinetic transformation provides a valuable approach to access axially atropisomers. This review summarizes seminal contributions recent advancements on this topic based the use different types reagents.
Язык: Английский
Процитировано
6
Science China Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Окт. 30, 2024
Язык: Английский
Процитировано
6
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3089 - 3099
Опубликована: Янв. 1, 2024
NHC and photocatalysis dual-catalyzed mono/difluoromethylative acylation of 1,3-enynes was realized, providing fluormethyl-substituted allenyl ketones. SO 2 might play a critical role in achieving high reactivity selectivity.
Язык: Английский
Процитировано
5
Nature Communications, Год журнала: 2024, Номер 15(1)
Опубликована: Окт. 16, 2024
The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis nitrogen-containing compounds. However, C-N have never been employed in cyclopropane. In this study, we use N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a reagent and photoredox catalyst dual-catalyzed 1,3-aminoacylation NHCs play multiple roles, functioning Lewis base catalysts to activate bonds, promoting oxidative quenching process PC*, acting efficient acyl radical transfer formation C-C bonds. between excited-state PC* NHC adduct key photooxidation generality aryl cyclopropanes.
Язык: Английский
Процитировано
4
Chemical Communications, Год журнала: 2024, Номер 60(54), С. 6837 - 6846
Опубликована: Янв. 1, 2024
Axially chiral biaryl ethers and related compounds hold valuable potential in natural products, medicinal chemistry, catalysis; however, their asymmetric syntheses have always been overlooked compared to other biaryl/hetero-biaryl atropisomers. Unlike the later class molecules bearing a single axis, former category possesses unique type of atropisomerism two axes. Due great importance diverse research domains, catalytic atropselective ether synthesis has recently witnessed an upsurge. This highlight article provides elaborated view on developments synthetic methods that explored achieve dual axial chirality scaffolds.
Язык: Английский
Процитировано
3