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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...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2022
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| 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 |
| _version_ | 1784688599227170816 |
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| author | Shaw, Paul Hassell-Hart, Storm J. Douglas, Gayle E. Malcolm, Andrew G. Kennedy, Alan R. White, Gemma V. Paterson, Laura C. Kerr, William J. |
| author_facet | Shaw, Paul Hassell-Hart, Storm J. Douglas, Gayle E. Malcolm, Andrew G. Kennedy, Alan R. White, Gemma V. Paterson, Laura C. Kerr, William J. |
| author_sort | Shaw, Paul |
| collection | PubMed |
| description | [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. |
| format | Online Article Text |
| id | pubmed-9016766 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-90167662022-04-20 Oxygenated Cyclopentenones via the Pauson–Khand Reaction of Silyl Enol Ether Substrates Shaw, Paul Hassell-Hart, Storm J. Douglas, Gayle E. Malcolm, Andrew G. Kennedy, Alan R. White, Gemma V. Paterson, Laura C. Kerr, William J. Org Lett [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. American Chemical Society 2022-04-04 2022-04-15 /pmc/articles/PMC9016766/ /pubmed/35377671 http://dx.doi.org/10.1021/acs.orglett.2c00856 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Shaw, Paul Hassell-Hart, Storm J. Douglas, Gayle E. Malcolm, Andrew G. Kennedy, Alan R. White, Gemma V. Paterson, Laura C. Kerr, William J. Oxygenated Cyclopentenones via the Pauson–Khand Reaction of Silyl Enol Ether Substrates |
| title | Oxygenated Cyclopentenones via the Pauson–Khand
Reaction of Silyl Enol Ether Substrates |
| title_full | Oxygenated Cyclopentenones via the Pauson–Khand
Reaction of Silyl Enol Ether Substrates |
| title_fullStr | Oxygenated Cyclopentenones via the Pauson–Khand
Reaction of Silyl Enol Ether Substrates |
| title_full_unstemmed | Oxygenated Cyclopentenones via the Pauson–Khand
Reaction of Silyl Enol Ether Substrates |
| title_short | Oxygenated Cyclopentenones via the Pauson–Khand
Reaction of Silyl Enol Ether Substrates |
| title_sort | oxygenated cyclopentenones via the pauson–khand
reaction of silyl enol ether substrates |
| url | 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 |
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