Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 10, Pages 1937-1949Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201547
Keywords
Synthetic methods; Chiral pool; Sustainable chemistry; Iodoetherification; Radical dehalogenation; Glycals
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Funding
- Fonds Europeen de Developpement Regional (FEDER)
- Centre National de la Recherche Scientifique (CNRS)
- Region Nord Pas-de-Calais
- Ministere de l'Education Nationale de l'Enseignement Superieur et de la Recherche
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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.
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