Palladium-Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides

Hervé Clavier (1) , Aymeric Lepronier (1) , Nathalie Bengobesse-Mintsa (1) , David Gatineau (1) , Hélène Pellissier (1) , Laurent Giordano (1) , Alphonse Tenaglia (1) , Gérard Buono (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

An efficient palladium-catalyzed [2 + 1]cycloaddition between ynamides and norbornenes or norbornadienes is reported. Both phosphapalla- dacycles and palladium/secondary phosphine oxide catalytic systems were found to be competent for the transformation allowing the preparation of ami- nomethylenecyclopropanes. The reaction showed general applicability to various functionalized bicyclo[2.2.1]hept-2-enes and ynamides. A chiral phosphapalladacycle was tested to carry out this transformation in an enantioselective fashion.

Mots clés: cycloaddition; cyclopropanes; norbor- nenes; palladium; phosphorus; ynamides

Domaines: Chimie organique; Catalyse

Hervé Clavier, Aymeric Lepronier, Nathalie Bengobesse-Mintsa, David Gatineau, Hélène Pellissier, et al.. Palladium-Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides. Advanced Synthesis and Catalysis, 2013, 355 (2-3), pp.403-408. ⟨10.1002/adsc.201200903⟩. ⟨hal-01409285⟩