Stephens, Thomas C. and Unsworth, William P. orcid.org/0000-0002-9169-5156 (2020) Consecutive Ring-Expansion Reactions for the Iterative Assembly of Medium-Sized Rings and Macrocycles. Synlett. pp. 133-146. ISSN 0936-5214
Abstract
Macrocycles and medium-sized rings have important applications in several scientific fields but can be challenging to make using traditional end-to-end cyclization reactions. Ring-expansion methods represent a useful alternative and offer numerous practical benefits. In this Account, we discuss the current state of the art of ring-expansion strategies that have been applied consecutively. Such methods have the power to expedite the design and synthesis of functionalized macro cycles via the selective, iterative insertion of smaller fragments into ring-enlarged products. 1 Introduction 2 Insertion Reactions 2.1 Transamidation/Transpeptidation 2.2 Transesterification 2.3 Transthioesterification 2.4 Aminyl Radical Cascade 2.5 Iterative Synthesis of Lactones 2.6 Successive Ring Expansion of β-Ketoesters and Lactams 3 Pericyclic Reactions 3.1 Sulfur-Mediated Rearrangements 3.2 Nitrogen-Mediated Rearrangements 4 Fragmentation Reactions 5 Conclusions and Future Outlook.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 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: | iterative synthesis,macro-cycles,medium-sized rings,rearrangements,ring enlargement,ring expansion |
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: | 04 Feb 2020 12:50 |
Last Modified: | 15 Feb 2025 00:08 |
Published Version: | https://doi.org/10.1055/s-0037-1611500 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1055/s-0037-1611500 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:156470 |
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Filename: SYNLETT_iterative_synthesis_cluster_paper_version_11_revision.docx
Description: SYNLETT iterative synthesis cluster paper version 11 revision