Iodoetherification of Isosorbide-Derived Glycals: Access to a Variety of O-Alkyl or O-Aryl Isosorbide Derivatives

A set of O-alkylated or O-arylated beta-iodo ethers has been synthesized from isosorbide. Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. The key step was the iodoetherification of isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.