This review covers the recent advances in the synthesis of enantiomerically pure
hydroxylamine’s employing nitrones as starting materials. Nucleophilic additions of organometallic
reagents to nitrones are the most common way for introducing a hydroxyamino
group into carbon skeletons with the concomitant formation of a new carbon-carbon bond.
Addition of nucleophiles derived from enolates, cyanide or fluorinated derivatives allows the
preparation of complex structures. Radical additions and, in particular samarium diiodidemediated
reductive coupling of nitrones with carbonyl compounds and α,β-unsaturated esters
have also been considered. All these approaches provide efficient methods of preparation of
enantiomerically pure hydroxylamine’s that are valuable synthetic intermediates.
Keywords: Hydrocyanation, hydroxylamines, mannich reaction, nitrones, organometallics, reductive coupling.
Rights & PermissionsPrintExport