Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)(3)/LiI system as the promoter

Thibaut Chalopin (1) , Khaoula Jebali (1, 2) , Catherine Gaulon-Nourry (3) , Fabrice Denes (1) , Jacques Lebreton (1) , Monique Mathé-Allainmat (1)

1 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
2 University of Tunis El Manar
3 IMMM - Institut des Molécules et Matériaux du Mans

The rapid and regioselective synthesis of a series of 2,6-disubstituted dihydropyranic building-blocks bearing an oxygenated side chain is described. The corresponding 4-iodo tetrahydropyran precursors, easily prepared by Prins cyclization, underwent regioselective elimination in the presence of an In(OAc)(3)/LiI system to provide the title compounds. The one-pot Prins cyclization-elimination process was also studied and could be achieved with the TMSBr/Lil/In(OAc)(3) system. (C) 2015 Elsevier Ltd. All rights reserved.

Mots clés: Oxygen heterocycles; Prins cyclization; Lewis acid; Elimination; Regioselectivity

Domaines: Chimie

Thibaut Chalopin, Khaoula Jebali, Catherine Gaulon-Nourry, Fabrice Denes, Jacques Lebreton, et al.. Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)(3)/LiI system as the promoter. Tetrahedron, 2016, 72 (2), pp.318-327. ⟨10.1016/j.tet.2015.11.046⟩. ⟨hal-02141568⟩