Microwave-assisted domino access to C2-chain functionalized furans from tertiary propargyl vinyl ethers

Tertiary propargyl vinyl ethers armed with an electron-withdrawing group (amide or ester) at the tertiary propargylic position have been efficiently transformed into trisubstituted C2-chain functionalized furans. The metal-free domino transformation involves a microwave-assisted tandem [3,3]-proparg...

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Detalles Bibliográficos
Autores: Tejedor, David, Cotos, Leandro, García-Tellado, Fernando
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2011
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/132565
Acceso en línea:http://hdl.handle.net/10261/132565
Access Level:acceso abierto
Descripción
Sumario:Tertiary propargyl vinyl ethers armed with an electron-withdrawing group (amide or ester) at the tertiary propargylic position have been efficiently transformed into trisubstituted C2-chain functionalized furans. The metal-free domino transformation involves a microwave-assisted tandem [3,3]-propargyl Claisen rearrangement/5-exo-dig O-cyclization reaction. The manifold can be performed in a one-pot fashion from the primary components (1,2-ketoester/1,2-ketoamide or tertiary propargyl alcohols). © 2011 American Chemical Society.