Work

Enantioselective synthesis of chiral N-arylpyrroles through photoinduced desymmetrization

Year: 2025

Type: article

Abstract: The C–N axial chirality is widely present in natural products, bioactive molecules, and chiral ligands. Catalytic asymmetric construction of C–N axially chiral compounds is a challenging task due to the lower rotational barriers of the C–N bond. Here, we report catalytic asymmetric Minisci reaction of prochiral N -arylpyrroles with α -amino acid-derived redox-active esters to produce enantiomerically enriched N -arylpyrroles with a C–N axis by dual photoredox and chiral phosphoric acid catalysis. The desymmetrization strategy achieved a variety of N -arylpyrroles with generally good diastereo- and enantioselectivities. A photoinduced desymmetrization protocol for the construction of chiral N -arylpyrroles with a C–N axis is described.

Source: Green Synthesis and Catalysis

DOI: 10.1016/j.gresc.2025.03.001

Authors: Zi-Wei He, Dong Liang, Jia-Rong Chen, Ying Cheng, Wen-Jing Xiao

Institution: Central China Normal University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, National Key Research and Development Program of China

Awards: G2682957140, G4210604088, G6855975958