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Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis

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JournalChemistry - A European Journal
DateAccepted/In press - 17 Nov 2015
DateE-pub ahead of print - 7 Jan 2016
DatePublished (current) - 2016
Volume22
Number of pages14
Early online date7/01/16
Original languageEnglish

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.

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© 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.

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