Chiral separation of substituted phenylalanine analogues using chiral palladium phosphine complexes with enantioselective liquid-liquid extraction

B.J.V. Verkuijl, B. Schuur, A.J. Minnaard, J.G. Vries, de, B.L. Feringa

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Abstract

Chiral palladium phosphine complexes have been employed in the chiral separation of amino acids and phenylalanine analogues in particular. The use of (S)-xylyl-BINAP as a ligand for the palladium complex in enantioselective liquid–liquid extraction allowed the separation of the phenylalanine analogues with the highest operational selectivity reported to date. 31P NMR, FTIR, FIR, UV-Vis, CD and Raman spectroscopy methods have been applied to gain insight into the binding mechanism of the amino acid substrates with the chiral palladium phosphine complexes. A complexation in a bidentate fashion is proposed.
Original languageEnglish
Pages (from-to)3045-3054
JournalOrganic & Biomolecular Chemistry
Volume8
Issue number13
DOIs
Publication statusPublished - 2010

Fingerprint

phosphine
Liquid-Liquid Extraction
phenylalanine
Palladium
Phenylalanine
phosphines
palladium
analogs
amino acids
Liquids
liquids
Amino Acids
Raman Spectrum Analysis
Fourier Transform Infrared Spectroscopy
Complexation
spectroscopy
Raman spectroscopy
selectivity
Nuclear magnetic resonance
Ligands

Cite this

Verkuijl, B.J.V. ; Schuur, B. ; Minnaard, A.J. ; Vries, de, J.G. ; Feringa, B.L. / Chiral separation of substituted phenylalanine analogues using chiral palladium phosphine complexes with enantioselective liquid-liquid extraction. In: Organic & Biomolecular Chemistry. 2010 ; Vol. 8, No. 13. pp. 3045-3054.
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Chiral separation of substituted phenylalanine analogues using chiral palladium phosphine complexes with enantioselective liquid-liquid extraction. / Verkuijl, B.J.V.; Schuur, B.; Minnaard, A.J.; Vries, de, J.G.; Feringa, B.L.

In: Organic & Biomolecular Chemistry, Vol. 8, No. 13, 2010, p. 3045-3054.

Research output: Contribution to journalArticleAcademicpeer-review

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AU - Verkuijl, B.J.V.

AU - Schuur, B.

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AU - Vries, de, J.G.

AU - Feringa, B.L.

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AB - Chiral palladium phosphine complexes have been employed in the chiral separation of amino acids and phenylalanine analogues in particular. The use of (S)-xylyl-BINAP as a ligand for the palladium complex in enantioselective liquid–liquid extraction allowed the separation of the phenylalanine analogues with the highest operational selectivity reported to date. 31P NMR, FTIR, FIR, UV-Vis, CD and Raman spectroscopy methods have been applied to gain insight into the binding mechanism of the amino acid substrates with the chiral palladium phosphine complexes. A complexation in a bidentate fashion is proposed.

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