Oxygenated Cyclopentenones via the Pauson–Khand Reaction of Silyl Enol Ether Substrates

[Image: see text] We report here the application of silyl enol ether moieties as efficient alkene coupling partners within cobalt-mediated intramolecular Pauson–Khand reactions. This cyclization strategy delivers synthetically valuable oxygenated cyclopentenone products in yields of ≤93% from both k...

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Detalles Bibliográficos
Autores principales: Shaw, Paul, Hassell-Hart, Storm J., Douglas, Gayle E., Malcolm, Andrew G., Kennedy, Alan R., White, Gemma V., Paterson, Laura C., Kerr, William J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9016766/
https://www.ncbi.nlm.nih.gov/pubmed/35377671
http://dx.doi.org/10.1021/acs.orglett.2c00856
Descripción
Sumario:[Image: see text] We report here the application of silyl enol ether moieties as efficient alkene coupling partners within cobalt-mediated intramolecular Pauson–Khand reactions. This cyclization strategy delivers synthetically valuable oxygenated cyclopentenone products in yields of ≤93% from both ketone- and aldehyde-derived silyl enol ethers, incorporates both terminal and internal alkyne partners, and delivers a variety of decorated systems, including more complex tricyclic structures. Facile removal of the silyl protecting group reveals oxygenated sites for potential further elaboration.

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