Fascione, Martin Anthony orcid.org/0000-0002-0066-4419, Brabham, Robin and Turnbull, W. Bruce (2016) Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis. Chemistry - A European Journal. ISSN 1521-3765
Abstract
The utility of sulfoxides in a diverse range of transformations in the field of carbohydrate chemistry has seen rapid growth since the first introduction of a sulfoxide as a glycosyl donor in 1989. Sulfoxides have since developed into more than just anomeric leaving groups, and today have multiple roles in glycosylation reactions. These include as activators for thioglycosides, hemiacetals, and glycals, and as precursors to glycosyl triflates, which are essential for stereoselective β-mannoside synthesis, and bicyclic sulfonium ions that facilitate the stereoselective synthesis of α-glycosides. In this review we highlight the mechanistic investigations undertaken in this area, often outlining strategies employed to differentiate between multiple proposed reaction pathways, and how the conclusions of these investigations have and continue to inform upon the development of more efficient transformations in sulfoxide based carbohydrate synthesis.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016, The Authors. This content is made available by the publisher under a Creative Commons Attribution Licence. This means that a user may copy, distribute and display the resource providing that they give credit. Users must adhere to the terms of the licence. |
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: | 02 Mar 2016 15:00 |
Last Modified: | 16 Oct 2024 12:44 |
Published Version: | https://doi.org/10.1002/chem.201503504 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/chem.201503504 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:93061 |
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