TY - JOUR
T1 - A combinatorial approach to recognition of chirality
T2 - preparation of highly enantioselective aryl-dihydropyrimidine selectors for chiral HPLC
AU - Lewandowski, Kevin
AU - Murer, Peter
AU - Svec, Frantisek
AU - Fréchet, Jean M.J.
PY - 1999
Y1 - 1999
N2 - A parallel library of 108 4-aryl-1,4-dihydropyrimidine (DHPM) enantiomers, which are potential selectors for chiral HPLC separations, was synthesized using the single-step Biginelli multicomponent condensation. The individual compounds were screened by observing the enantioselectivity for resolution on a "brush-type" L-(3,5-dinitrobenzoyl)leucine-based chiral stationary phase, and separation factors a up to 12 were achieved. The best candidates from the library contained an ortho-substituted aromatic group at C4 carbon atom of the pyrimidine ring and an alkyl substituent at NI nitrogen atom. Resolution of the enantiomers of the lead compound, 4-(9-phenanthryl)-DHPM 8, using semipreparative chiral HPLC followed by attachment to monodisperse macroporous aminomethacrylate beads, provided the novel polymer based chiral stationary phase with good enantioselectivities in the resolution of several π-acidic aryl-dihydropyrimidines and derivatized profens. In addition, 3,5-dinitrobenzamido derivatives of α-amino acids could be resolved under normal phase HPLC conditions with separation factors up to 8.
AB - A parallel library of 108 4-aryl-1,4-dihydropyrimidine (DHPM) enantiomers, which are potential selectors for chiral HPLC separations, was synthesized using the single-step Biginelli multicomponent condensation. The individual compounds were screened by observing the enantioselectivity for resolution on a "brush-type" L-(3,5-dinitrobenzoyl)leucine-based chiral stationary phase, and separation factors a up to 12 were achieved. The best candidates from the library contained an ortho-substituted aromatic group at C4 carbon atom of the pyrimidine ring and an alkyl substituent at NI nitrogen atom. Resolution of the enantiomers of the lead compound, 4-(9-phenanthryl)-DHPM 8, using semipreparative chiral HPLC followed by attachment to monodisperse macroporous aminomethacrylate beads, provided the novel polymer based chiral stationary phase with good enantioselectivities in the resolution of several π-acidic aryl-dihydropyrimidines and derivatized profens. In addition, 3,5-dinitrobenzamido derivatives of α-amino acids could be resolved under normal phase HPLC conditions with separation factors up to 8.
UR - http://www.scopus.com/inward/record.url?scp=0032600765&partnerID=8YFLogxK
U2 - 10.1021/cc980014p
DO - 10.1021/cc980014p
M3 - Article
C2 - 10746018
AN - SCOPUS:0032600765
SN - 1520-4766
VL - 1
SP - 105
EP - 112
JO - Journal of Combinatorial Chemistry
JF - Journal of Combinatorial Chemistry
IS - 1
ER -