A Chiral Recognition Model for the Chromatographic Resolution of N-Acylated 1-Aryl-1-aminoalkanes

Article abstract of DOI:10.1021/jo00173a045

The enantiomers of N-acyl derivatives of 1-aryl-1-aminoalkanes generally may be chromatographically separated on a silica-bonded chiral stationary phase derived from N-(3,5-dinitrobenzoyl)phenylglycine.Chiral recognition is enhanced by increases in either the ? basicity of the aryl substituent or the size of the alkyl substituent but is diminished by increases in the size of the acyl group.Carbamate and urea derivatives of these amines are also resolvable.Chiral recognition models are proposed to account for the observed chiral recognition and are used to assign absolute configuration to several acylated amines.