A facile and rapid preparation of hydroxamic acids by hydroxylaminolysis using DBU as base. Issue 20 (18th May 2016)

• Record Type: Journal Article
• Authors: Beillard, Audrey; Bhurruth-Alcor, Yushma; Bouix-Peter, Claire; Bouquet, Karinne; Chambon, Sandrine; Clary, Laurence; Harris, Craig S.; Millois, Corinne; Mouis, Grégoire; Ouvry, Gilles; Pierre, Romain; Reitz, Arnaud; Tomas, Loic
• Is Part Of: Tetrahedron letters. Volume 57:Issue 20(2016)
• Page Start: 2165
• Page End: 2170
• Publication Date: 2016-05-18
• Subjects: Hydroxylaminolysis -- Hydroxamic acid formation -- DBU; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.003
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An efficient process to prepare hindered hydroxamic acids from esters is proposed. Quickest reaction times and best yields were observed when using DBU as the base. A chromatography-free process using recyclable PS-DBU is also disclosed. No epimerisation occured when usingl -phenylalanine methyl ester as the substrate. Abstract: While there are many protocols for the preparation of hydroxamic acids from their corresponding carboxylic acid or carboxylic ester precursors, most use strong mineral bases that can lead to carboxylic acid impurities that can be difficult to remove using standard chromatographic techniques. This problem is exacerbated when the carbonyl group is hindered. Herein, we communicate a robust hydroxylaminolysis protocol for the preparation of hydroxamic acids in high yield and purity.