Selective hydrogenolysis of benzyl ethers in the presence of benzylidene acetals with Raney nickel

Aurélie Vincent (1) , Joëlle Prunet (1)

1 DCSO - Laboratoire de synthèse organique

A simple method to remove selectively a benzyl group protecting a hydroxyl function in the presence of a benzylidene acetal by catalytic hydrogenolysis with Raney nickel is reported. This method was successfully applied to the synthesis of the C1–C14 fragment of dolabelides.

Mots clés: Catalytic hydrogenation; benzyl; benzylidene acetal; 4-methoxybenzyl; deprotection; dolabelide

Domaines: Chimie organique

Aurélie Vincent, Joëlle Prunet. Selective hydrogenolysis of benzyl ethers in the presence of benzylidene acetals with Raney nickel. Tetrahedron Letters, 2006, 47, pp.4075. ⟨10.1016/j.tetlet.2006.03.189⟩. ⟨hal-00087139⟩