Cited by N-heterocyclic carbene-catalyzed atroposelective synthesis of axially chiral 5-aryl 2-pyrones from enals

Recent advances in organocatalytic atroposelective reactions DOI

Henrich Szabados,

Radovan Šebesta

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 55 - 121

Published: Jan. 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.

Language: Английский

Citations

Divergent Synthesis of Axially Chiral 2-Pyranones and Fused 2-Pyridones via N-Heterocyclic Carbene-Catalyzed Atroposelective [3 + 3] Annulation DOI

Z. Liu, Chenxing Li,

Simiao Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 24, 2025

An N-heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of alkynyl acylazoliums with benzothiazole derivatives has been developed for the divergent synthesis axially chiral triaryl 2-pyranones and fused 2-pyridones. The regioselectivity this protocol depends on structure benzothiazoles three different nucleophilic centers. obtained frameworks represent a new class arylheterocycle atropisomers, which may be potentially useful in medicinal chemistry.

Language: Английский

Citations

N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of Pyrrolo[3,4-b]pyridines with Configurationally Stable C–N Axial Chirality DOI

Yunpeng Chu,

Meng Wu,

Fang Hu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(21), P. 3884 - 3889

Published: May 24, 2022

The first atroposelective synthesis of pyrrolo[3,4-b]pyridines catalyzed by N-heterocyclic carbene has been achieved. A wide range chiral atropisomers were obtained in high yields with excellent enantioselectivities (96-99% enantiomeric excess). experimental results and density functional theory calculations showed that the C-N axial chirality product had thermal stability.

Language: Английский

Citations

Kinetic Resolution Approach to the Synthesis of C–N Axially ChiralN-Aryl Aminomaleimides via NHC-Catalyzed [3 + 3] Annulation DOI

Soumen Barik,

Rohan Chandra Das,

Kuruva Balanna

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(29), P. 5456 - 5461

Published: July 20, 2022

Chiral NHC-catalyzed kinetic resolution of N-aryl aminomaleimides allowing the synthesis C-N axially chiral via remote chirality control is presented. The catalytically generated α,β-unsaturated acylazoliums from 2-bromoenals underwent selective [3 + 3] annulation with one enantiomers maleimide to furnish fused-dihydropyridinone (bearing axial/central chirality, up 6:1 dr, >99:1 er) leaving enantioenriched opposite enantiomer (up er). Studies on bond rotation barrier and dependence temperature are also provided.

Language: Английский

Citations

N-heterocyclic carbene-catalyzed atroposelective synthesis of axially chiral 5-aryl 2-pyrones from enals DOI

Guanjie Wang,

Juhui Huang,

Linxue Zhang

et al.

Science China Chemistry, Journal Year: 2022, Volume and Issue: 65(10), P. 1953 - 1961

Published: Sept. 13, 2022

Language: Английский

Citations