Jk. Dutton et al., SYNTHESIS ELF 17H-TETRAHENZO[A,C,G,I]FLUORENE DERIVATIVES AS CHIRAL SELECTORS FOR ENANTIOMERIC SEPARATION BY HPLC ON POROUS GRAPHITIZED CARBON, Journal of the Chemical Society. Perkin transactions. I, (20), 1995, pp. 2581-2587
The synthesis of the amides 2 which are designed to be selectors conta
ining the chiral N-(3,5-dinitrobenzoyl)-alpha-phenylglycine covalently
linked to tetrabenzo[a,c,g,i]fluorene is described. These amides are
strongly adsorbed onto porous graphitised carbon, which affords chiral
stationary phases that are able to resolve both racemic aromatic alco
hols 3 and the methyl esters of Fmoc amino acids 4 on microgram quanti
ties using high-pressure liquid chromatography. Two methods of prepara
tion of these chiral phases from 2 and porous graphitised carbon are d
escribed and the stability of these phases to the chromatographic cond
itions and to water have also been investigated.