Han, J., Hoteite, L. and Harrity, J.P.A. orcid.org/0000-0001-5038-5699 (2022) Development of an enantioselective allylic alkylation of acyclic α-fluoro-β-ketoesters for the asymmetric synthesis of 3-fluoropiperidines. Chemistry – A European Journal, 28 (56). e202201595. ISSN 0947-6539
Abstract
The first usefully-enantioselective Pd-catalyzed asymmetric allylic alkylation of α-fluoro-β-ketoesters has been achieved using the Trost family of chiral ligands providing products in up to 92% ee. This work provides new insights that can address the typically modest selectivities associated with acyclic α-fluoroenolates, and provides experimental evidence that the typically poor levels of enantiocontrol associated with these systems is not necessarily due to the presence of E/Z enolate mixtures. Finally, this methodology allows useful 3-fluoropiperidine intermediates to be easily prepared, and we demonstrate that these systems are amenable to a range of functionalization reactions leading to new building blocks for the discovery of bioactive products.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/4.0/) which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
Keywords: | enantioselective; Catalysis; palladium; piperidine; functionalization |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Funding Information: | Funder Grant number EUROPEAN COMMISSION - HORIZON 2020 721223 |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 05 Aug 2022 11:05 |
Last Modified: | 03 Feb 2023 14:24 |
Status: | Published |
Publisher: | Wiley |
Refereed: | Yes |
Identification Number: | 10.1002/chem.202201595 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:189075 |