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High‐performance liquid chromatography of imine stereoisomers on cellulose‐based chiral stationary phases
Author(s) -
Willems Johannes G. H.,
Duchateau Alexander L. L.,
Zwanenburg Binne
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:8<727::aid-chir3>3.0.co;2-2
Subject(s) - chemistry , imine , enantiomer , derivatization , isomerization , chirality (physics) , chiral column chromatography , chromatography , organic chemistry , schiff base , high performance liquid chromatography , enantiomeric excess , cellulose , enantioselective synthesis , stereochemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.