Synthesis and palladium-catalysed isomerisation of fused polycyclic tetrahydrofurans : efficient and stereoselective one-pot domino construction of functionalised bridged bicyclo[n.2.1] ring systems

Pierre-Yves Roger (1) , Fabien Blondeau (1) , David Bensa (1) , Thierry Constantieux (1) , Jean Rodriguez (1)

1 STeRéO

A new one-pot domino reaction for a general entry to functionalised bridged bicyclo[n.2.1] ring systems from α,α'-diactivated cyclic ketones and trans-1,4-dihalides is described. The sequence combines a base promoted C-O cycloalkylation reaction leading to fused polycyclic enol ethers and their in situ palladium-catalysed isomerisation.

Mots clés: Vinyltetrahydrofurans; Palladium-catalysed Isomérisation; Bicyclo[2.2.1]heptanone Bicyclo[3.2.1]octanone; Bicyclo[4.2.1]nonanone

Domaines: Chimie organique

Pierre-Yves Roger, Fabien Blondeau, David Bensa, Thierry Constantieux, Jean Rodriguez. Synthesis and palladium-catalysed isomerisation of fused polycyclic tetrahydrofurans : efficient and stereoselective one-pot domino construction of functionalised bridged bicyclo[n.2.1] ring systems. Molecular Diversity, 2009, 13, pp.469-473. ⟨10.1007/s11030-009-9131-2⟩. ⟨hal-00681054⟩