Clarke, Paul Andrew orcid.org/0000-0003-3952-359X, Alomari, Khadra, Chakravarthy, Sai Pavan et al. (2 more authors) (2022) Enantioselective “Clip-Cycle” Synthesis of Di-, Tri- and Spiro- Substituted Tetrahydropyrans. Organic and Biomolecular Chemistry. pp. 1181-1185. ISSN 1477-0539
Abstract
-Unsaturated alcohols were “clipped” via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity. The mechanism and origin of the enantioselectivity was probed by DFT calculations and kinetic isotope studies, where there was excellent correlation between the computational and synthetic investigations
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Royal Society of Chemistry 2022. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 17 Jan 2022 12:10 |
Last Modified: | 16 Oct 2024 18:09 |
Published Version: | https://doi.org/10.1039/D2OB00023G |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1039/D2OB00023G |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:182621 |