Synthesis of Chiral Axially Diaryl Aldehydes by Chiral Phosphoric Acid Catalyzed Desymmetrization Reaction DOI

Lutong Yuan,

Lixin Cui,

Yuheng Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract Axially chiral biaryl aldehydes are precursors for the synthesis of axially compounds and novel catalysts great interest, which play vital roles in extensive research fields. However, limited strategies exist efficient aldehydes, construction structurally diverse remains challenging. Herein, a strategy is reported with varying structures from dialdehydes aromatic amines presence phosphoric acid catalyst. This protocol features excellent enantioselectivity, mild conditions, good functional‐group tolerance.

Language: Английский

Recent advances in organocatalytic atroposelective reactions DOI Creative Commons

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

1
Development of Configurationally Labile Biaryl Reagents for Atropisomer Synthesis DOI
Changhui Wu, Jin Yang,

Xiaoyuan Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(28)

Published: May 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.

Language: Английский

Citations

6
Disclosing the mechanism and origin of stereoselectivity of the NHC-catalyzed transformation reaction of enals with acyl azolium as a key intermediate DOI

Pingxin Liang,

Dongying Shi, Yang Wang

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(15), P. 4302 - 4310

Published: Jan. 1, 2024

The reaction mechanism and origin of stereoselectivity the NHC-catalyzed transformation an acyl azolium intermediate have been theoretically investigated using DFT method.

Language: Английский

Citations

5
Asymmetric construction of axial and planar chirality with N-heterocyclic carbene (NHC) organocatalysis DOI
Meng Zhang,

Xiaoqun Yang,

Xiaolin Peng

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Language: Английский

Citations

4
Synthesis of Chiral Axially Diaryl Aldehydes by Chiral Phosphoric Acid Catalyzed Desymmetrization Reaction DOI

Lutong Yuan,

Lixin Cui,

Yuheng Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract Axially chiral biaryl aldehydes are precursors for the synthesis of axially compounds and novel catalysts great interest, which play vital roles in extensive research fields. However, limited strategies exist efficient aldehydes, construction structurally diverse remains challenging. Herein, a strategy is reported with varying structures from dialdehydes aromatic amines presence phosphoric acid catalyst. This protocol features excellent enantioselectivity, mild conditions, good functional‐group tolerance.

Language: Английский

Citations

0