Effect of multivalency on the performance of enantioselective separation media for chiral HPLC prepared by linking multiple selectors to a porous polymer support via aliphatic dendrons

Frank H. Ling, Victor Lu, Frantisek Svec, Jean Frechet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

Chiral stationary phases (CSPs) containing L-proline indananilide chiral selectors attached through a multivalent dendritic linker to monodisperse macroporous poly(2-hydroxyethyl methacrylate-co-ethylene dimethacrylate) beads have been prepared using two different approaches. The convergent method involves the preparation of ligands in solution and their subsequent attachment to the support. The divergent approach is based on the stepwise "on-bead" formation of the linker using methods that are typical of solid-phase synthesis. While the convergent CSPs feature well-defined ligands, their loading is relatively low. In contrast, the divergent technique affords CSPs with higher loading but with more limited control over precise ligand architecture. Excellent enantioselectivities characterized by separation factors of up to 31 were achieved for the separation of racemic N-(3,5-dinitrobenzoyl)-α-amino acid alkyl amides with these new CSPs under normal-phase HPLC conditions.

Original languageEnglish (US)
Pages (from-to)1993-2002
Number of pages10
JournalJournal of Organic Chemistry
Volume67
Issue number7
DOIs
StatePublished - Apr 5 2002

ASJC Scopus subject areas

  • Organic Chemistry

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