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Proceeding Paper

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

by
Christophe Berini
1,
Aurélie Lavergne
2,
Valérie Molinier
3,
Stéphane Lebrun
2,
Jean-Marie Aubry
2 and
Eric Deniau
2,*
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.
†
Presented at the 23rd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2019; Available online: https://ecsoc-23.sciforum.net/.
Proceedings 2019, 41(1), 62; https://doi.org/10.3390/ecsoc-23-06489
Published: 14 November 2019
(This article belongs to the Proceedings of The 23rd International Electronic Conference on Synthetic Organic Chemistry)
Versions Notes

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.
Keywords: isosorbide; glycal; iodoetherification; β-iodo ethers; radical dehalogenation isosorbide; glycal; iodoetherification; β-iodo ethers; radical dehalogenation

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MDPI and ACS Style

Berini, C.; Lavergne, A.; Molinier, V.; Lebrun, S.; Aubry, J.-M.; Deniau, E. Asymmetric Iodoetherification of Isosorbide-Derived Glycals: A Regio- and Stereoselective Access to a Variety of O-Substituted Isosorbide Derivatives. Proceedings 2019, 41, 62. https://doi.org/10.3390/ecsoc-23-06489

AMA Style

Berini C, Lavergne A, Molinier V, Lebrun S, Aubry J-M, Deniau E. Asymmetric Iodoetherification of Isosorbide-Derived Glycals: A Regio- and Stereoselective Access to a Variety of O-Substituted Isosorbide Derivatives. Proceedings. 2019; 41(1):62. https://doi.org/10.3390/ecsoc-23-06489

Chicago/Turabian Style

Berini, Christophe, Aurélie Lavergne, Valérie Molinier, Stéphane Lebrun, Jean-Marie Aubry, and Eric Deniau. 2019. "Asymmetric Iodoetherification of Isosorbide-Derived Glycals: A Regio- and Stereoselective Access to a Variety of O-Substituted Isosorbide Derivatives" Proceedings 41, no. 1: 62. https://doi.org/10.3390/ecsoc-23-06489

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