Oxygenated cyclopentenones via the pauson-khand reaction of silyl enol ether substrates

Shaw, Paul and Hassell-Hart, Storm J. and Douglas, Gayle E. and Malcolm, Andrew G. and Kennedy, Alan R. and White, Gemma V. and Paterson, Laura C. and Kerr, William J. (2022) Oxygenated cyclopentenones via the pauson-khand reaction of silyl enol ether substrates. Organic Letters, 24 (14). pp. 2750-2755. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.2c00856)

[thumbnail of Shaw-etal-OL-2022-Oxygenated-cyclopentenones-via-the-Pauson-Khand-reaction]
Preview
 Text. Filename: Shaw_etal_OL_2022_Oxygenated_cyclopentenones_via_the_Pauson_Khand_reaction.pdf
Final Published Version
License: Creative Commons Attribution 4.0 logo
Download (934kB)| Preview

Abstract

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.

ORCID iDs

Shaw, Paul, Hassell-Hart, Storm J. ORCID logoORCID: https://orcid.org/0000-0002-5028-5409, Douglas, Gayle E., Malcolm, Andrew G. ORCID logoORCID: https://orcid.org/0000-0003-4235-917X, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, White, Gemma V. ORCID logoORCID: https://orcid.org/0000-0002-8868-2872, Paterson, Laura C. and Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X;
  • Item type:Article
    ID code:80138
    Dates:
    Date
    Event
    15 April 2022
    Published
    4 April 2022
    Published Online
    31 March 2022
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:08 Apr 2022 09:06
    Last modified:18 Nov 2024 01:15
    URI:https://strathprints.strath.ac.uk/id/eprint/80138
CORE (COnnecting REpositories)