Unsworth, William P. orcid.org/0000-0002-9169-5156 and Taylor, Richard J K orcid.org/0000-0002-5880-2490 (2016) Direct Imine Acylation:A Versatile Method for the Synthesis of Nitrogen-Containing Heterocycles, Spirocycles and Natural Products. Synlett. pp. 2051-2064. ISSN 0936-5214
Abstract
Diverse nitrogen-containing heterocyclic compounds can be synthesised by the N-acylation of imines using functionalised carboxylic acids (Direct Imine Acylation, DIA). The carboxylic acids are activated in situ using the coupling agent propylphosphonic acid anhydride (T3P), before reacting with the imine coupling partner to generate N-acyliminium ions in situ, that can then be trapped by oxygen-, nitrogen-, sulfur- or carbon-based nucleophiles built into the carboxylic acid. This versatile, convergent method has been used to generate a wide range of products, including aromatic and aliphatic heterocycles, β-lactams, azaspirocycles and natural products. 1 Introduction 2 DIA in the Total Synthesis of ‘Upenamide 3 DIA with Benzoic Acid Derivatives 4 DIA with Aliphatic Carboxylic Acids 5 DIA in the Synthesis of β-Lactams 6 DIA in the Synthesis of Azaspirocycles 7 Mechanistic Studies 8 Conclusion
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016, Georg Thieme Verlag. 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 |
Keywords: | cavidine,evodiamine,N-acyliminium ions,N-heterocycles,natural products,spirocycles,‘upenamide |
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: | 25 May 2016 14:47 |
Last Modified: | 16 Oct 2024 13:03 |
Published Version: | https://doi.org/10.1055/s-0035-1562095 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1055/s-0035-1562095 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:100170 |
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