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Published on: October 29, 2013
Microwave-assisted domino access to C2-chain functionalized furans from tertiary propargyl vinyl ethers
David Tejedor1, Leandro Cotos, Fernando García-Tellado
1Departamento de Química Biológica y Biotecnología, Instituto de Productos Naturales y Agrobiología , CSIC, Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain. dtejedor@ipna.csic.es
Abstract:
Tertiary propargyl vinyl ethers armed with an electron-withdrawing group (amide or ester) at the tertiary propargylic position have been efficiently transformed into trisubstituted C(2)-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).
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