Catalytic Atroposelective Synthesis of C–N Axially Chiral Pyrazolyl Pyrroles via De Novo Construction of a Pyrrole Ring
Abstract
The catalytic atroposelective synthesis of five–five-membered C–N axially chiral heterobiaryls featuring the de novo construction of a pyrrole ring was reported. This chiral phosphoric-acid-catalyzed asymmetric Paal–Knorr reaction of 5-aminopyrazoles with 1,4-diketones delivered C–N axially chiral pyrazolyl pyrroles in good yields (up to 96%) with excellent enantioselectivities (up to 97% ee). This work establishes an efficient strategy for constructing five–five-membered C–N axially chiral pyrazole scaffolds and enriches the family of C–N axially chiral molecules.
Fields of Study & Subjects
Axial and Atropisomeric Chirality Synthesis
Asymmetric Synthesis and Catalysis
Synthesis and Properties of Aromatic Compounds
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 4
- Pages
- 1481–1486
- Publication date
- 20 January 2026
- Language
- EN