Grogan, Gideon James orcid.org/0000-0003-1383-7056, Orukotan, Will, Palate, Kleopas et al. (7 more authors) (2024) Divergent Cascade Ring Expansion Reactions of Acryloyl Imides. Chemistry : A European Journal. e202303270. ISSN 0947-6539
Abstract
Macrocyclic and medium-sized ring ketones, lactones and lactams can all be made from common acryloyl imide starting materials via divergent, one-pot cascade ring expansion reactions. Following either conjugate addition with an amine or nitromethane, or osmium(VIII) catalysed dihydoxylation, rearrangement via a 4-atom ring expansion takes place spontaneously to form the ring expanded products. A second ring expansion can also be performed following a second iteration of imide formation and alkene functionalisation/ring expansion. In the dihydroxylation series, 3- or 4-atom ring expansion can be performed selectively, depending on whether the reaction is under kinetic or thermodynamic control.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2023 The Authors. |
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: | 27 Nov 2023 10:30 |
Last Modified: | 26 Jun 2025 12:00 |
Published Version: | https://doi.org/10.1002/chem.202303270 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/chem.202303270 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:205960 |
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Description: Chemistry A European J - 2023 - Orukotan - Divergent Cascade Ring‐Expansion Reactions of Acryloyl Imides
Licence: CC-BY 2.5