Highly Selective Syn Addition of 1,3-Diones to Internal Ynamides Catalyzed by Zinc Iodide

Rémi Plamont (1) , Lionel V. Graux (1) , Hervé Clavier (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

Having previously established that 1,3-diones could be used as nucleophiles to perform additions to ynamides, highly selective hydroalkoxylation of internal ynamides is now described herein. Several catalytic systems were compared to carry out this transformation including transition metal-based catalysts or Lewis acids. ZnI2 was found to be both very active and highly selective giving only E adducts through a syn addition. Scope and limits investigation showed that this catalyst was compatible with various functional groups. In addition to 17 examples of ynamide hydroalkoxylation, one example of ynamide hydroarylation is reported.

Domaines: Chimie organique; Catalyse

Rémi Plamont, Lionel V. Graux, Hervé Clavier. Highly Selective Syn Addition of 1,3-Diones to Internal Ynamides Catalyzed by Zinc Iodide. European Journal of Organic Chemistry, 2018, 2018 (11), pp.1372-1376. ⟨10.1002/ejoc.201701690⟩. ⟨hal-01768371⟩