Dearomative Nucleophilic Addition of Lithium Enolates to Electron‐Poor Indoles
The dearomatization of electron-poor indoles was investigated through the addition of lithiated ester or ketone enolates. Nitro-substituted indoles undergo 1,4-addition to afford the dearomatized products, after smooth hydrolysis. Indoles bearing an α-ketoamide group show a more complex reactivity, undergoing either 1,2- or 1,4-addition, depending on the steric hindrance of the amide group. The regioselectivity of the latter is buttressed by DFT calculations.
Authors
- Matthieu Hédouin
- Isabelle Chataigner (ORCID: https://orcid.org/0000-0001-6302-7831)
- Mélanie Roseau (ORCID: https://orcid.org/0000-0003-0162-351X)
- Catherine Fressigné (ORCID: https://orcid.org/0000-0002-3101-6385)
- Julien Legros (ORCID: https://orcid.org/0000-0002-4807-7897)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Sorbonne Université (FR)
- Laboratoire de Chimie Théorique (FR)
- Normandie Université (FR)
- Université de Rouen Normandie (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
Publication Details
- Journal
- ChemPhysChem
- Published
- 2025-11-04
- DOI
- https://doi.org/10.1002/cphc.202500522
- Primary Topic
- Coordination Chemistry and Organometallics
- Type
- article
- Field-Weighted Citation Impact
- 0.00