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Hydrogenative Cyclopropanation and Hydrogenative Metathesis

MPS-Authors
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Peil,  Sebastian
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Guthertz,  Alexandre
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Biberger,  Tobias
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

ange201904256-sup-0001-misc_information.pdf
(Supplementary material), 11MB

Citation

Peil, S., Guthertz, A., Biberger, T., & Fürstner, A. (2019). Hydrogenative Cyclopropanation and Hydrogenative Metathesis. Angewandte Chemie International Edition, 58(26), 8851-8856. doi:10.1002/anie.201904256.


Cite as: http://hdl.handle.net/21.11116/0000-0003-E7A1-2
Abstract
The unusual geminal hydrogenation of a propargyl alcohol derivative with [CpXRuCl] as the catalyst entails formation of pianostool ruthenium carbenes in the first place; these reactive intermediates can be intercepted with tethered alkenes to give either cyclopropanes or cyclic olefins as the result of a formal metathesis event. The course of the reaction is critically dependent on the substitution pattern of the alkene trap.