Sengoden, Mani, North, Michael orcid.org/0000-0002-6668-5503 and Whitwood, Adrian C. (2019) Synthesis of Oxazolidinones by using Carbon Dioxide as a C1 Building Block and an Aluminium-Based Catalyst. ChemSusChem. ISSN 1864-564X
Abstract
Oxazolidinone synthesis through the coupling of carbon dioxide and aziridines was catalysed by an aluminium(salphen) complex at 50–100 °C and 1–10 bar pressure under solvent-free conditions. The process was applicable to a variety of substituted aziridines, giving products with high regioselectivity. It involved the use of a sustainable and reusable aluminium-based catalyst, used carbon dioxide as a C1 source and provided access to pharmaceutically important oxazolidinones as illustrated by a total synthesis of toloxatone. This protocol was scalable, and the catalyst could be recovered and reused. A catalytic cycle was proposed based on stereochemical, kinetic and Hammett studies.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019 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. author accepted manuscript publisher on 29 May 2019 |
Keywords: | aluminium catalysis,aziridines,carbon dioxide fixation,oxazolidinones,Schiff bases |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 15 Jul 2019 14:30 |
Last Modified: | 01 Jan 2025 00:09 |
Published Version: | https://doi.org/10.1002/cssc.201901171 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1002/cssc.201901171 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:148611 |
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Filename: chemsuschem_aziridines_revised.docx
Description: chemsuschem aziridines revised