Ring-rearrangement metathesis of 3,6-dialkoxy-3,6-dihydro-2H-pyrans

Morgan Donnard (1) , Théophile Tschamber , Sandy Desrat (2) , Karen Hinsinger , Jacques Eustache

1 COB - Laboratoire de Chimie organique et bioorganique
2 ICSN - Institut de Chimie des Substances Naturelles

The first RCM–ROM–RCM sequence using a non-strained heterocycle as relay moiety is described. The course of the reaction strongly depends on the nature and relative configuration of the substituents in the starting trienic system. In addition, for a productive reaction to be observed, the site of initiation of the metathesis cascade is crucial. The compounds thus obtained may be useful for the synthesis of unusual polydeoxydisaccharides.

Mots clés: Metathesis reaction; Saccharides; Cascade; Domino; RRM

Domaines: Chimie organique; Catalyse

Morgan Donnard, Théophile Tschamber, Sandy Desrat, Karen Hinsinger, Jacques Eustache. Ring-rearrangement metathesis of 3,6-dialkoxy-3,6-dihydro-2H-pyrans. Tetrahedron Letters, 2008, 49 (7), pp.1192-1195. ⟨10.1016/j.tetlet.2007.12.047⟩. ⟨hal-01265871⟩