High-performance liquid chromatography of imine stereoisomers on cellulose-based chiral stationary phases

• Published in: Chirality (New York, N.Y.) Vol. 9; no. 8; pp. 727 - 731
• Main Authors: Willems, Johannes G. H., Duchateau, Alexander L. L., Zwanenburg, Binne
• Format: Journal Article
• Language: English
• Published: New York Alan R. Liss, Inc 1997
• Subjects: 5-dimethylphenylcarbamate; amylose tris; amylose tris(3,5‐dimethylphenylcarbamate); cellulose tris; cellulose tris(3,5‐dimethylphenylcarbamate); cellulose tris(4-methylbenzoate); chiral HPLC; e.e. determination; imine enantiomers; imine isomerization reaction
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/(SICI)1520-636X(1997)9:8<727::AID-CHIR3>3.0.CO;2-2

A high‐performance liquid chromatographic method has been developed for the analysis of the intermediate imines and end products in an asymmetric isomerization route toward optically active amines. Separation of the imine enantiomers was performed on commercially available Chiralcel OD‐H, Chiralcel OJ, and Chiralpak AD chiral stationary phases. All substituted imine enantiomers could be readily resolved with selectivities (α) higher than 1.10 using the Chiralpak AD column. By derivatization with ring‐substituted benzaldehydes, aromatic amines were converted into Schiff base derivatives and the enantiopurity of these amines was determined. Chirality 9:727–731, 1997. © 1997 Wiley‐Liss, Inc.