Hydroxamate-directed access to β-Kdo glycosides

Chem Commun (Camb). 2023 Aug 15;59(66):10028-10031. doi: 10.1039/d3cc02609d.

Abstract

The reaction repertoire for forming transient aziridinone or azaoxyallyl cations from α-halohydroxamate is conceptually extended to design Kdo-glycosyl donors by installing the hydroxamate moiety at an anomeric centre, which is shown to be highly effective for stereoselective access to β-Kdo glycosides. The pivotal roles of hydroxamate over amide are revealed in control experiments.