The enantiomers of 17 alpha-hydroxybenzylphosphonate diethylesters containing para, or ortho substituents or other aromatic rings (1-naphthyl, 2-naphthyl, and 2-thienyl) have been successfully separated by HPLC on a Whelk-O 1 chiral stationary phase which is superior to other CSPs. The effect of the substituents, particularly halogens, on the enantioselectivity was investigated and related to a chiral recognition model. The absolute configurations of 4-methyl and 2-methyl substituted alpha-hydroxybenzylphosphonates were obtained by measurement of the circular dichroism spectra of the isolated enantiomers. (C) 1998 Wiley-Liss, Inc.
Separation of the enantiomers of alpha-hydroxybenzylphosphonate esters by enantioselective HPLC and determination of their absolute configuration by circular dichroism
FAILLA, Salvatore;
1998-01-01
Abstract
The enantiomers of 17 alpha-hydroxybenzylphosphonate diethylesters containing para, or ortho substituents or other aromatic rings (1-naphthyl, 2-naphthyl, and 2-thienyl) have been successfully separated by HPLC on a Whelk-O 1 chiral stationary phase which is superior to other CSPs. The effect of the substituents, particularly halogens, on the enantioselectivity was investigated and related to a chiral recognition model. The absolute configurations of 4-methyl and 2-methyl substituted alpha-hydroxybenzylphosphonates were obtained by measurement of the circular dichroism spectra of the isolated enantiomers. (C) 1998 Wiley-Liss, Inc.File in questo prodotto:
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