Asymmetric iodoetherification of isosorbide-derived glycals: A regio- and stereoselective access to a variety of O‑substituted isosorbide derivatives

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. A set of O‑alkyl‑ or O‑arylated beta‑iodo ethers has been synthesized from isosorbide. 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.