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Synthesis of Trisubstituted Furans from Epoxypropargyl Esters by Sequential SmI2-Promoted Reduction-Elimination and Pd(II)-Catalyzed Cycloisomerization

José M. Aurrecoechea, Elena Pérez and Mónica Solay

*Hétérochimie Fondamentale et Appliquée (UMR 5069 CNRS), Université Paul-Sabatier, 118 route de Narbonne, 31062 Toulouse Cédex, France

J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem., 2001, 66, 564-569.

DOI: 10.1021/jo0014257


SmI2 promotes a formation of unstable 2,3,4-trien-1-ols from 4,5-epoxyalk-2-ynyl esters via reduction and elimination of an acetate or benzoate leaving group. A subsequent Pd(II)-catalyzed cycloisomerization provides furans in the presence of a proton source. The whole one-pot sequence takes place under mild reaction conditions and tolerates some useful functional groups.

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proposed reaction pathway and catalytic cycle for Pd-catalyzed cycloisomerization

Key Words

furans, samarium diiodide

ID: J42-Y2001