Work

Dearomative Nucleophilic Addition of Lithium Enolates to Electron‐Poor Indoles

Year: 2025

Type: article

Abstract: 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.

Source: ChemPhysChem

DOI: 10.1002/cphc.202500522

Authors: Mélanie Roseau, Matthieu Hédouin, Catherine Fressigné, Julien Legros, Isabelle Chataigner