Regioselective Michael-induced cyclisation of γ- and δ-hydroxy vinyl sulfides and vinyl dithiocarbamates

V. Aucagne (1) , C. Lorin (2) , A. Tatibouët (1) , P. Rollin (1)

1 ICOA - Institut de Chimie Organique et Analytique
2 CEA - Commissariat à l'énergie atomique et aux énergies alternatives

We herein describe the unprecedented use of heteroaryl vinyl sulfides and vinyl dithiocarbamates as hetero-Michael addition acceptors. Combined chelating and electron-withdrawing effects are postulated to stabilise the transient anionic species and allow smooth Michael-induced ring closure to produce diversely functionalised C-glycosides.

Domaines: Sciences du Vivant [q-bio]

V. Aucagne, C. Lorin, A. Tatibouët, P. Rollin. Regioselective Michael-induced cyclisation of γ- and δ-hydroxy vinyl sulfides and vinyl dithiocarbamates. Tetrahedron Letters, 2005, 46 (25), pp.4349-4352. ⟨10.1016/j.tetlet.2005.04.112⟩. ⟨hal-02086017⟩