A facile circular dichroism protocol for rapid determination of enantiomeric excess and concentration of chiral primary amines.

ABSTRACT: A protocol for the rapid determination of the absolute configuration and enantiomeric excess (ee) of alpha-chiral primary amines with potential applications in asymmetric reaction discovery has been developed. The protocol requires derivatization of alpha-chiral primary amines through condensation with pyridine carboxaldehyde to quantitatively yield the corresponding imine. The Cu(I) complex with 2,2'-bis (diphenylphosphino)-1,1'-dinaphthyl (BINAP--Cu(I)) with the imine yields a metal-to-ligand charge-transfer (MLCT) band in the visible region of the circular dichroism (CD) spectrum upon binding. Diastereomeric host-guest complexes give CD signals of the same signs but different amplitudes, allowing for differentiation of enantiomers. Processing the primary optical data from the CD spectru

SUBMITTER: Nieto S 

PROVIDER: S-EPMC2982703 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature