Palladium-Catalysed Isomerisation of 2-Vinylidenehydrofurans into 1,3-Dienes and some Aspects of their Reactivity

Abdelkader Ghobsi (1) , Salih Hacini (1) , Laurence Wavrin (1) , Anouk Gaudel-Siri (2) , Agnès Corbères (1) , Cyril Nicolas (1) , Damien Bonne (1) , Jacques Viala (1) , Jean Rodriguez (1)

1 STeRéO
2 ISM2 - Institut des Sciences Moléculaires de Marseille

The transformation of easily accessible 2-vinylidenehydrofurans into stable 1,3-dienes has been achieved by using catalytic amounts of palladium(0). These valuable compounds were then engaged in subsequent Diels-Alder reactions giving access to complex heterocyclic cores found in numerous natural products. A rationale for the regioselectivity of the Diels-Alder reactions with vinylfurans has been provided by DFT calculations.

Mots clés: Palladium; Allenes; Isomerization; Diels-Alder reactions

Domaines: Chimie organique

Abdelkader Ghobsi, Salih Hacini, Laurence Wavrin, Anouk Gaudel-Siri, Agnès Corbères, et al.. Palladium-Catalysed Isomerisation of 2-Vinylidenehydrofurans into 1,3-Dienes and some Aspects of their Reactivity. European Journal of Organic Chemistry, 2008, pp.4446-4453. ⟨10.1002/ejoc.200800517⟩. ⟨hal-00677026⟩