Enantioselective Synthesis of Benzazepine Bearing a Diaryl Quaternary Carbon Center by Aryl Iodide-Catalyzed Asymmetric Desymmetrization
Abstract
Chiral benzazepines are commonly found in a variety of bioactive molecules; however, efficient and modular approaches for constructing medium-sized rings remain challenging. Herein, we report an enantioselective synthesis of benzazepines bearing a diaryl quaternary carbon center via aryl iodide-catalyzed desymmetrization of 4,4-diarylpentanamides through asymmetric oxidative C-H amination, wherein chiral hypervalent iodine species serve as an alternative to transition-metal catalysts. The reaction features mild conditions, high yields, and excellent enantioselectivities (up to 97:3 er). Furthermore, the synthetic utility of this method has been demonstrated by scale-up synthesis and a series of synthetic transformations.
Fields of Study & Subjects
Axial and Atropisomeric Chirality Synthesis
Asymmetric Synthesis and Catalysis
Coordination Chemistry and Organometallics
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 26
- Pages
- 8451–8456
- Publication date
- 19 June 2026
- Language
- EN