Diversity-Oriented Functionalization of Cyclodienes Through Selective Cycloaddition/Ring-Opening/Cross-Metathesis Protocols; Transformation of a Flatland into Three-Dimensional Scaffolds with Stereo-and Regiocontrol

Kiss, Loránd and Benke, Zsanett and Remete, Attila M. and Fülöp, Ferenc (2020) Diversity-Oriented Functionalization of Cyclodienes Through Selective Cycloaddition/Ring-Opening/Cross-Metathesis Protocols; Transformation of a Flatland into Three-Dimensional Scaffolds with Stereo-and Regiocontrol. CHEMICAL RECORD, 20 (10). pp. 1129-1141. ISSN 1527-8999 (print); 1528-0691 (online)

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Abstract

This article presents selective transformations of some readily available cyclodienes through simple chemical procedures into novel functionalized small-molecular entities. The syntheses hereby described involved selective cycloadditions, followed by ring-opening metathesis of the resulting beta-lactam or isoxazoline derivatives and selective cross-metathesis by differentiation of the olefin bonds on the alkenylated heterocycles. The cross-metathesis transformations have been detailed, which were performed under various experimental conditions with the aim of exploring chemodiscrimination of the olefin bonds and delivering the corresponding functionalized beta-lactam or isoxazoline derivatives.

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