title: Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines.
abstract: A simple three-component chiral derivatization protocol for determining the enantiopurity of chiral primary amines by 1H NMR spectroscopic analysis is described here. The method involves condensation of the amines with 2-formylphenylboronic acid and enantiopure 1,1'-bi-2-naphthol. This approach affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by the integration of well-resolved diastereotopic resonances in their 1H NMR spectra, thus enabling the enantiopurity of the parent amine to be determined easily. The protocol, as described, takes less than 90 min to complete.
authors.affiliation: Department of Chemistry, University of Bath, Bath BA2 7AY, UK.
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Pérez-Fuertes
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Kelly
authors.forename: John S
authors.initials: JS
authors.lastname: Fossey
authors.forename: Magdalena E
authors.initials: ME
authors.lastname: Powell
authors.forename: Steven D
authors.initials: SD
authors.lastname: Bull
authors.forename: Tony D
authors.initials: TD
authors.lastname: James
mesh_terms: D000588:Amines / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism; D001547:Benzaldehydes / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry / Q000378:metabolism; D001897:Boronic Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry
chemical_list: C532809:2-formylphenylboronic acid; D000588:Amines; C406944:BINOL, naphthol; D001547:Benzaldehydes; D001596:Benzylamines; D001897:Boronic Acids; D004952:Esters; D009284:Naphthols; C412332:1,1'-bi-2-naphthol