Chiral recognition: Design and preparation of chiral stationary phases using selectors derived from Ugi multicomponent condensation reactions and a combinatorial approach

Enugurthi Brahmachary, Frank H. Ling, Frantisek Svec, Jean M.J. Fréchet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Combinatorial approaches together with high-throughput screening have been used to develop highly selective stationary phases for chiral recognition. Libraries of potential chiral selectors have been prepared by the Ugi multicomponent condensation reactions and screened for their enantioselectivity using the reciprocal approach involving a chiral stationary phase with immobilized model target compound N-(3,5-dinitrobenzoyl)-α-L-leucine. The best candidates were identified from the library of phenyl amides of 2-oxo-azetidineacetic acid derivatives. This screening also enabled specification of the functionalities of the selector desired to achieve the highest level of chiral recognition. The substituents of the phenyl ring adjacent to the chiral center of the selector candidates exhibited the most profound effect on the chiral recognition. The best candidate was then synthesized on a larger scale, resolved into single enantiomers using preparative enantioselective HPLC, and attached to porous poly(2-hydroxyethyl methacrylate-co-ethylene dimethacrylate) beads via an ester linkage to afford the desired stationary phase. Selectivities α as high as 3.2 were found for the separation of a variety of amino acid derivatives.

Original languageEnglish (US)
Pages (from-to)441-450
Number of pages10
JournalJournal of Combinatorial Chemistry
Volume5
Issue number4
DOIs
StatePublished - Jul 1 2003

ASJC Scopus subject areas

  • Chemistry(all)

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