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Issue 20, 2018
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Dual roles of ynoates: desymmetrization of dicarboxylic acids using trialkylamines as alkyl equivalents

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Abstract

A novel method has been developed for the desymmetrization of aromatic dicarboxylic acids by employing an esterification reaction/conjugate addition of a carboxyl group to ynoates, which can trigger a coupling reaction. This one-pot cascade transformation, utilizing trialkylamines as alkyl sources for esterification, and ethyl propiolate as a protective or coupling reagent for carboxyl functions (hydrolysis, amidation, esterification, and thioesterification), leads to an asymmetric dicarbonyl target skeleton in a selective manner.

Graphical abstract: Dual roles of ynoates: desymmetrization of dicarboxylic acids using trialkylamines as alkyl equivalents

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Publication details

The article was received on 24 Aug 2018, accepted on 12 Sep 2018 and first published on 13 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00919H
Citation: Org. Chem. Front., 2018,5, 2955-2959
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    Dual roles of ynoates: desymmetrization of dicarboxylic acids using trialkylamines as alkyl equivalents

    X. Xu, L. Huang, X. Yin, E. V. Van der Eycken and H. Feng, Org. Chem. Front., 2018, 5, 2955
    DOI: 10.1039/C8QO00919H

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