Fascione, M, Brabham, R and Turnbull, WB (2016) Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis. Chemistry - A European Journal, 22 (12). pp. 3916-3928. ISSN 0947-6539
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. Published by Wiley-VCH Verlag GmbH & Co KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
Keywords: | carbohydrates; glycosylation; mechanism; organic synthesis; sulfoxides |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 04 Dec 2015 12:52 |
Last Modified: | 25 Apr 2016 13:46 |
Published Version: | http://dx.doi.org/10.1002/chem.201503504 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/chem.201503504 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:92520 |