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Updated: Oct 8, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Photo-Fries-type rearrangement of cyclic enamides. An efficient route to structurally diverse five-membered
Piotr Szcześniak1, Bartłomiej Furman1
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw 01-224, Poland. pszczesniak@icho.edu.pl.
Abstract:
A simple, efficient and user-friendly protocol for the preparation of structurally diverse enaminones from enamides has been developed. The strategy is based on a photo-induced intramolecular Fries-type rearrangement. The photochemical transformation proceeds under mild reaction conditions, applies to a broad substrate range, is highly economic, and limits the amount of waste produced. The proposed methodology was used as a key step in the synthesis of dihydrojasmone an important fragrance compound.
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