Das, A., Choi, A. and Coldham, I. orcid.org/0000-0003-4602-6292 (2023) Photocatalysis and kinetic resolution by lithiation to give enantioenriched 2-arylpiperazines. Organic Letters, 25 (6). pp. 987-991. ISSN 1523-7060
Abstract
Piperazines are important heterocycles in drug compounds. We report the asymmetric synthesis of arylpiperazines by photocatalytic decarboxylative arylation (metallaphotoredox catalysis) then kinetic resolution using n-BuLi/(+)-sparteine. This gave a range of piperazines with very high enantioselectivities. Further functionalizations gave enantioenriched 2,2-disubstituted piperazines, and either N-substituent can be removed selectively. Late-stage functionalizations of enantioenriched piperazine derivatives were demonstrated, including synthesis of a drug compound with glycogen synthase kinase (GSK)-3β inhibitor activity with potential for treating Alzheimer’s disease.
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Copyright, Publisher and Additional Information: | © 2023 The Authors. This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. | ||||
Keywords: | Humans; Piperazines; Alzheimer Disease; Kinetics; Phosphorylation; Catalysis | ||||
Dates: |
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Institution: | The University of Sheffield | ||||
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) | ||||
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Depositing User: | Symplectic Sheffield | ||||
Date Deposited: | 28 Feb 2023 10:35 | ||||
Last Modified: | 28 Feb 2023 10:35 | ||||
Status: | Published | ||||
Publisher: | American Chemical Society (ACS) | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1021/acs.orglett.3c00074 | ||||
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