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14 November 2019

Asymmetric Iodoetherification of Isosorbide-Derived Glycals: A Regio- and Stereoselective Access to a Variety of O-Substituted Isosorbide Derivatives †

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1
ORIL Industrie, 13 rue Auguste Desgenetais, 76200 Bolbec, France
2
University Lille, CNRS, Centrale Lille, ENSCL, University Artois, UMR 8181-UCCS—Unité de Catalyse et Chimie du Solide, F-59000 Lille, France
3
Total Exploration Production, Pôle d’Etudes et de Recherche de Lacq, B.P. 47, 64170 Lacq, France
*
Author to whom correspondence should be addressed.
Proceedings2019, 41(1), 62;https://doi.org/10.3390/ecsoc-23-06489
This article belongs to the Proceedings The 23rd International Electronic Conference on Synthetic Organic Chemistry
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Abstract

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.

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