om8b00819_si_001.pdf (18.28 MB)
Application of Polysaccharide-Based Chiral HPLC Columns for Separation of Nonenantiomeric Isomeric Mixtures of Organometallic Compounds
journal contribution
posted on 2018-12-20, 12:18 authored by Masamichi Ogasawara, Yuuki Enomoto, Mizuho Uryu, Xicheng Yang, Ayami Kataoka, Atsushi OhnishiA series
of polysaccharide-based chiral stationary phase (CSP) columns, Daicel
Chiralpak IA, IB, and IC, were applied in the separation of the nonenantiomeric
isomers of various organometallic compounds and were found to be highly
effective in recognizing isomers of minor structural differences.
The CSP columns have succeeded to separate the double-bond regioisomers
in bridged (η5-formylcyclopentadienyl)manganese(I)
dicarbonyl complexes 1a/1b, the structural
isomers of methylbutenylferrocene derivatives in 2a/2b and 3a/3b, and the geometrical
isomers of the (2-methyl-2-butenyl)ferrocenes in (Z)/(E)-3b. Due to the close similarity
of the isomeric compounds in these mixtures, separations of the components
are extremely difficult and could not be attained by conventional
methods such as silica gel column chromatography, silica gel HPLC,
recrystallization, distillation/sublimation, etc. Clearly, the polysaccharide-based
CSP columns have unique advantages in separation/purification technology,
and this study has shown potential usefulness of the CSP columns in
separation of not only enantiomeric but also nonenantiomeric mixtures.