Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

A diiodo ruthenium olefin metathesis pre‐catalyst was employed to achieve remarkably selective cross‐metathesis reactions of prenylated 1,6‐dienes, effectively overcoming the entropically favored intramolecular ring‐closing metathesis. This reaction was investigated using Density Functional Theory (...

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Published inAngewandte Chemie International Edition p. e202412430
Main Authors Iudanov, Keren, Nechmad, Noy Bracha, Poater, Albert, Lemcoff, N. Gabriel
Format Journal Article
LanguageEnglish
Published 21.09.2024
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Summary:A diiodo ruthenium olefin metathesis pre‐catalyst was employed to achieve remarkably selective cross‐metathesis reactions of prenylated 1,6‐dienes, effectively overcoming the entropically favored intramolecular ring‐closing metathesis. This reaction was investigated using Density Functional Theory (DFT) computations and fine‐tuned through the application of a Design of Experiments (DoE) approach. The potential of this innovative process was demonstrated through the unprecedented functionalization of various terpene natural products via cross‐metathesis, resulting in the synthesis of new derivatives in a single step.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202412430