Separation of the enantiomers of α‐hydroxybenzylphosphonate esters by enantioselective HPLC and determination of their absolute configuration by circular dichroism | Zendy

Caccamese Salvatore | Zendy; Failla Salvatore | Zendy; Finocchiaro Paolo | Zendy; Principato Grazia | Zendy

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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.

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