ISSN:
0899-0042
Keywords:
enantioseparation
;
chiral stationary phase
;
HPLC
;
amylose phenylcarbamate
;
chiral discrimination
;
resolution
;
enantiomer
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Four 4-halogen-substituted phenylcarbamate derivatives of amylose were prepared and their chiral recognition abilities as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were evaluated and compared with those of the corresponding cellulose derivatives. The amylose derivatives with fluoro, chloro, bromo, or iodo group at the four-position on the phenyl group were found to show higher chiral resolving ability than the corresponding cellulose derivatives. Among four amylose derivatives 4-fluoro- and 4-chlorophenylcarbamates showed an excellent chiral recognition ability. Especially, amylose tris(4-chlorophenylcarbamate) resolved (±)-1,2,2,2-tetraphenylethanol with a very high α value (α = 8.29). In order to obtain useful information concerning the chiral recognition mechanism of this resolution, we also performed enantioseparation of a variety of analogous racemic alcohols, and found that both the hydroxy and bulky triphenylmethyl groups of the racemate are essential for the effective chiral recognition. Chirality 9:63-68, 1997. © 1997 Wiley-Liss, Inc.
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
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