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Updated: Jun 27, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Metal-mediated cyclization of aryl and benzyl glycidyl ethers: a complete scenario
Rocío Marcos1, Carles Rodríguez-Escrich, Clara I Herrerías
1Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain.
Abstract:
Enantiomerically pure aryl and benzyl glycidyl ethers undergo stereospecific cyclizations leading to 3-chromanols or to tetrahydrobenzo[c]oxepin-4-ols under mild conditions in the presence of a catalytic amount of FeBr3/3AgOTf. The same processes are also mediated, albeit in a much less efficient manner, by AuCl3/3AgOTf. The set of active mediators in this group of processes (BF3 x Et2O, FeBr3, FeBr3/3AgOTf, AuCl3/3AgOTf) shows its nature as Friedel-Crafts reactions and disfavors the intermediacy of arylgold species.
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