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

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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