Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones

We report a new catalytic protocol for the synthesis of γ,δ-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass...

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Detalles Bibliográficos
Autores: Gómez-Suárez, Adrián, Gasperini, Danila, Vummaleti, Sai Vikrama Chaitanya, Poater Teixidor, Albert, Cavallo, Luigi, Nolan, Steven P.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2014
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/10346
Acceso en línea:http://hdl.handle.net/10256/10346
Access Level:acceso embargado
Palabra clave:Cetones -- Síntesi
Ketones -- Synthesis
Descripción
Sumario:We report a new catalytic protocol for the synthesis of γ,δ-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated