Enantioselective Pd-Catalyzed Electrochemical Dearomative Allylation of Tropones: Construction of All-C Quaternary Stereocenters
Abstract
High Resolution Image Download MS PowerPoint Slide A Pd-catalyzed electroreductive enantioselective dearomatization of tropones is documented. High levels of chemoselectivity toward the formation of seven-membered ring ketones featuring a stereochemically controlled all-carbon α-stereocenter are successfully accomplished by means of a Tsuji–Trost-like process (24 examples, regioselectivity >25:1, enantiomeric ratio of up to 96:4). Computational and electrochemical analyses allowed elucidation of the reaction manifold that involves initial reduction of the tropone motif and a subsequent chemo- and enantioselective allylation via an outer-sphere approach. In this way, a novel concept for the dearomatization of electron-poor scaffolds is disclosed by means of electrochemical reductive umpolung.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 13
- Pages
- 4227–4233
- Publication date
- 18 March 2026
- Language
- EN