A safe and scalable synthesis of 2-hydroxy-3-alkoxypropionates by epoxide ring opening. Issue 34 (19th August 2015)

• Record Type: Journal Article
• Authors: Waring, Michael J.; Bennett, Stuart N.L.; Campbell, Leonie; Hallam, Stephen; Martin, Nathaniel G.; Tickner, Christopher
• Is Part Of: Tetrahedron letters. Volume 56:Issue 34(2015)
• Page Start: 4904
• Page End: 4907
• Publication Date: 2015-08-19
• Subjects: Catalysis -- Epoxides -- Lewis acids -- Magnesium -- Ring opening; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.080
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.