A convenient method for the conversion of N-acyloxazolidinones to hydroxamic acids.
Treatment of N-acyloxazolidinones with hydroxylamines using samarium triflate as a Lewis acid provides the corresponding hydroxamic acids in 50-98% yields at room temperature. The conversion proceeds with high degree of chemoselectivity and without racemization of chiral centers alpha- to the acyl group. [reaction: see text]
D006877:Hydroxamic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D013696:Temperature
D006877:Hydroxamic Acids; D008698:Mesylates; D023303:Oxazolidinones; C012077:trifluoromethanesulfonic acid