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Separation of the enantiomers of α‐hydroxybenzylphosphonate esters by enantioselective HPLC and determination of their absolute configuration by circular dichroism
Author(s) -
Caccamese Salvatore,
Failla Salvatore,
Finocchiaro Paolo,
Principato Grazia
Publication year - 1998
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/chir.17
Subject(s) - chemistry , enantiomer , circular dichroism , absolute configuration , chirality (physics) , enantioselective synthesis , chiral column chromatography , stereochemistry , high performance liquid chromatography , chiral stationary phase , halogen , chiral derivatizing agent , chromatography , organic chemistry , catalysis , chiral symmetry , physics , alkyl , quantum mechanics , nambu–jona lasinio model , quark
The enantiomers of 17 α‐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 α‐hydroxybenzylphosphonates were obtained by measurement of the circular dichroism spectra of the isolated enantiomers. Chirality 10:100–105, 1998. © 1998 Wiley‐Liss,Inc.