Chiral Lewis acid-Hydroxylamine Hybrid Reagent for enantioselective Michael addition reaction directed towards β-amino acids synthesis

We have succeeded in introducing a chiral auxiliary tethered by an appropriate metal into the hydroxy group of N-benzylhydroxylamine. The thus-obtained recyclable chiral reagent can act as an amine nucleophile to give chiral isoxazolidinones (up to 71% ee) as a β-amino acid synthon on the reaction with α,β-unsaturated carbonyl compounds.