Lawer, Aggie, Epton, Ryan G, Stephens, Thomas C et al. (7 more authors) (2020) Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion. Chemistry : A European Journal. pp. 1-11. ISSN 1521-3765
Abstract
The outcome of ring expansion reactions based on amino/hydroxyacid side chain insertion is strongly dependent on ring size. This manuscript, which builds upon our previous work on Successive Ring Expansion (SuRE) methods, details efforts to better define the scope and limitations of these reactions on lactam and β-ketoester ring systems with respect to ring size and additional functionality. The synthetic results provide clear guidelines as to which substrate classes are more likely to be successful and are supported by computational results, using a Density Functional Theory (DFT) approach. Calculating the relative Gibbs free energies of the three isomeric species that are formed reversibly during ring expansion enables the viability of new synthetic reactions to be correctly predicted in most cases. The new synthetic and computational results are expected to support the design of new lactam- and β-ketoester-based ring expansion reactions.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 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) |
Funding Information: | Funder Grant number EPSRC EP/P029795/1 |
Depositing User: | Pure (York) |
Date Deposited: | 28 May 2020 11:00 |
Last Modified: | 21 Jan 2025 17:47 |
Published Version: | https://doi.org/10.1002/chem.202002164 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1002/chem.202002164 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:161319 |