title: A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines.
abstract: A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by (1)H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.
authors: Department of Chemistry, University of Bath, Claverton Down, Bath, BA27AY, UK.
authors: David A
authors: DA
authors: Tickell
authors: Mary F
authors: MF
authors: Mahon
authors: Steven D
authors: SD
authors: Bull
authors: Tony D
authors: TD
authors: James
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D006898:Hydroxylamines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C532809:2-formylphenylboronic acid; C406944:BINOL, naphthol; D001547:Benzaldehydes; D001897:Boronic Acids; D004952:Esters; D006898:Hydroxylamines; D009284:Naphthols