Lookup NU author(s): Professor Mike Waring
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Epoxides are useful precursors for the synthesis of hydroxyl-bearing building blocks via Lewis acid catalyzed, nucleophilic ring opening. However, the reaction of glycidate esters with alcohol nucleophiles can be quite challenging with many of the classical paradigms for epoxide opening failing to give efficient reaction. In our hands, the most efficient catalyst described in the literature for effecting this transformation was magnesium perchlorate. However, ring opening of methyl glycidate with this catalyst revealed the potential for rapid and uncontrollable decomposition with onset at a relatively low temperature. Herein, the development of an alternative process, which is safe and scalable, is described. This allowed the synthesis of a series of novel 2-hydroxy-3-alkoxypropionates.
Author(s): Waring MJ, Bennett SNL, Campbell L, Hallam S, Martin NG, Tickner C
Publication type: Article
Publication status: Published
Journal: Tetrahedron Letters
Print publication date: 19/08/2015
Online publication date: 02/06/2015
Acceptance date: 25/06/2015
ISSN (print): 0040-4039
ISSN (electronic): 1873-3581
Publisher: Pergamon Press
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