Unified Photoredox-Catalyzed Aerobic Oxidative Dynamic Kinetic Asymmetric Transformation for C–N Atropoisomers Mediated by Chiral Organophosphites
The synthesis of anilides with a chiral C(═O)-N axis has relied on direct installation of the chiral C(sp<sup>2</sup>)-N(sp<sup>2</sup>) bond or enantioselective modification of the peripheral groups. However, these methods are constrained by the size and type of functional groups compatible with each strategy. Herein, we report a dynamic kinetic asymmetric transformation (DYKAT) for the aerobic oxidation of iminium ions to access C(═O)-N axial chirality that addresses those limitations. Furthermore, it eliminates the need for any auxiliary functional groups, which enables us to develop a unified method for the synthesis of atroposelective isoquinolone, lactam, and amide.
Authors
- Kumar Vanka (ORCID: https://orcid.org/0000-0001-7301-7573)
- Asish Bera
- Pradip Maity (ORCID: https://orcid.org/0000-0001-8493-3171)
- Priyam Bajpai (ORCID: https://orcid.org/0000-0002-6933-4741)
- Pinku Saikia (ORCID: https://orcid.org/0000-0002-3542-4167)
- Rajesh G. Gonnade (ORCID: https://orcid.org/0000-0002-2841-0197)
- Susmita Maity
- Arindam Saha (ORCID: https://orcid.org/0000-0002-0421-0633)
- M Aarthika
- Ayantika Bhattacharjya
Institutions
- National Chemical Laboratory (IN)
- Institute of Catalysis and Petrochemistry (RU)
- Material (Belgium) (BE)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c02273
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India
- Indian Institute of Science Education and Research Pune
- Science and Engineering Research Board
- National Chemical Laboratory