Straightforward one-pot stereoselective synthesis of substituted tetrahydrofurans from 1,3-butadienes and aldehydes.

Maryline Roux , Chahinez Aouf , Jean-Luc Parrain (1) , Maurice Santelli

1 STeRéO

A new and efficient multicomponent reaction involving a double-allylation sequence is reported. In situ generated bimetallic reagents are prepared from disilane and added onto a range of aliphatic aldehydes to afford a direct access to trisubstituted tetrahydrofurans in good to excellent diastereoselectivity (up to 70%).

Mots clés: tetrahydrofuran; 3-butadiene; multicomponent; allylation

Domaines: Chimie organique

Maryline Roux, Chahinez Aouf, Jean-Luc Parrain, Maurice Santelli. Straightforward one-pot stereoselective synthesis of substituted tetrahydrofurans from 1,3-butadienes and aldehydes.. Tetrahedron Letters, 2007, 48, pp.4011-4014. ⟨10.1016/j.tetlet.2007.04.034⟩. ⟨hal-00679642⟩