Regioselective Preparation of 7-Oxanorborna-2,5-diene-2,3-dicarboxylic Acid Derivatives by the Diels–Alder Reaction: A Selective Access to Furans by Retro-Diels–Alder Reaction

Nisrine Sultan; Régis Guillot; Luis Blanco; Sandrine Deloisy

doi:10.1055/s-0033-1338802

Synthesis, Table of Contents

Synthesis 2013; 45(14): 2018-2028
DOI: 10.1055/s-0033-1338802

paper

Regioselective Preparation of 7-Oxanorborna-2,5-diene-2,3-dicarboxylic Acid Derivatives by the Diels–Alder Reaction: A Selective Access to Furans by Retro-Diels–Alder Reaction

Nisrine Sultan

^aLaboratoire de Synthèse Organique et Méthodologie, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO, UMR 8182-CNRS), Bât. 420, Univ. Paris-Sud 11, 91405 Orsay Cedex, France Fax: +33(1)69156278 Email: sandrine.deloisy@u-psud.fr

,

Régis Guillot

^bService de Cristallographie, ICMMO (UMR 8182-CNRS), Bât. 420, Univ. Paris-Sud 11, 91405 Orsay Cedex, France

,

Luis Blanco

^aLaboratoire de Synthèse Organique et Méthodologie, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO, UMR 8182-CNRS), Bât. 420, Univ. Paris-Sud 11, 91405 Orsay Cedex, France Fax: +33(1)69156278 Email: sandrine.deloisy@u-psud.fr

,

Sandrine Deloisy*

^aLaboratoire de Synthèse Organique et Méthodologie, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO, UMR 8182-CNRS), Bât. 420, Univ. Paris-Sud 11, 91405 Orsay Cedex, France Fax: +33(1)69156278 Email: sandrine.deloisy@u-psud.fr

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Abstract

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Abstract

Hydrolysis of 1-substituted 7-oxanorborna-2,5-diene-2,3-dicarboxylates occurred regioselectively at the ester group in the 3-position to give monocarboxylic acids from which diesters containing two different alkoxy groups and amido esters were selectively prepared. Hydrogenation of these oxanorbornadiene derivatives followed by a retro-Diels–Alder reaction gave the corresponding furans as single regioisomers.

Key words

Diels–Alder reactions - hydrolyses - esters - amides - regioselectivity - furans - heterocycles

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References

References

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