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A safe and scalable synthesis of 2-hydroxy-3-alkoxypropionates by epoxide ring opening

Lookup NU author(s): Professor Mike Waring

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Abstract

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.


Publication metadata

Author(s): Waring MJ, Bennett SNL, Campbell L, Hallam S, Martin NG, Tickner C

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2015

Volume: 56

Issue: 34

Pages: 4904-4907

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

URL: http://dx.doi.org/10.1016/j.tetlet.2015.06.080

DOI: 10.1016/j.tetlet.2015.06.080


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