TY - JOUR
T1 - Efficient enantiorecognition of ruthenium(II) complexes by silica-bound teicoplanin
AU - Gasparrini, Francesco
AU - D'Acquarica, Ilaria
AU - Vos, Johannes G.
AU - O'Connor, Christine M.
AU - Villani, Claudio
PY - 2000/9/8
Y1 - 2000/9/8
N2 - A series of chiral tris-diimine ruthenium(II) complexes have been resolved by HPLC on a chiral stationary phase. The stationary phase (CSP1) was prepared by covalent attachment of the glycopeptide antibiotic teicoplanin to isocyanate activated silica gel. CSP1 selectively retains the enantiomers of [Ru(L)3]2+ (L=2,2'-bypyridine (bpy), 1,10-phenanthroline and 4,7-diphenyl-1,10-phenanthroline), with a preference for the Δ isomer. For the mixed-ligand complexes [Ru(bpy)2pztr]+ and [Ru(bpy)2pytr]+ (Hpztr=3-(pyrazin-2-yl)-1,2,4-triazole, Hpytr=3-(pyridin-2-yl)-1,2,4-triazole), where the triazole unit is bound to the metal centre either through the N2 or the N4 nitrogen of the ring, CSP1 discriminates both the enantiomers and the regioisomers. Diastereo- and enantioselective association was also observed between CSP1 and the stereoisomers of the dinuclear complex ((Ru(bpy)2)2bpt]3+ (Hbpt=3,5-bis(pyridin-2-yl)-1,2,4-triazole), with differences in binding affinities of 1.4 kJ/mol between the homochiral enantiomers. Copyright (C) 2000 Elsevier Science Ltd.
AB - A series of chiral tris-diimine ruthenium(II) complexes have been resolved by HPLC on a chiral stationary phase. The stationary phase (CSP1) was prepared by covalent attachment of the glycopeptide antibiotic teicoplanin to isocyanate activated silica gel. CSP1 selectively retains the enantiomers of [Ru(L)3]2+ (L=2,2'-bypyridine (bpy), 1,10-phenanthroline and 4,7-diphenyl-1,10-phenanthroline), with a preference for the Δ isomer. For the mixed-ligand complexes [Ru(bpy)2pztr]+ and [Ru(bpy)2pytr]+ (Hpztr=3-(pyrazin-2-yl)-1,2,4-triazole, Hpytr=3-(pyridin-2-yl)-1,2,4-triazole), where the triazole unit is bound to the metal centre either through the N2 or the N4 nitrogen of the ring, CSP1 discriminates both the enantiomers and the regioisomers. Diastereo- and enantioselective association was also observed between CSP1 and the stereoisomers of the dinuclear complex ((Ru(bpy)2)2bpt]3+ (Hbpt=3,5-bis(pyridin-2-yl)-1,2,4-triazole), with differences in binding affinities of 1.4 kJ/mol between the homochiral enantiomers. Copyright (C) 2000 Elsevier Science Ltd.
UR - https://www.scopus.com/pages/publications/0034622892
U2 - 10.1016/S0957-4166(00)00292-5
DO - 10.1016/S0957-4166(00)00292-5
M3 - Article
AN - SCOPUS:0034622892
SN - 0957-4166
VL - 11
SP - 3535
EP - 3541
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 17
ER -