Issue 13, 2010
From the journal:

Organic & Biomolecular Chemistry

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

Bastiaan J. V. Verkuijl,a   Boelo Schuur,b   Adriaan J. Minnaard,*a   Johannes G. de Vries*ac  and  Ben L. Feringa*a  

* Corresponding authors

a Laboratories for Organic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, Groningen, The Netherlands

b Eindhoven University of Technology, Department of Chemistry and Chemical Engineering, Den Dolech 2, Eindhoven, The Netherlands

c DSM Innovative Synthesis BV, P.O. Box 18, MD Geleen, The Netherlands

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.

Graphical abstract: Chiral separation of substituted phenylalanine analogues using chiral palladium phosphine complexes with enantioselective liquid–liquid extraction

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Article information

DOI
https://doi.org/10.1039/B924749A
Article type
Paper
Submitted
25 Nov 2009
Accepted
30 Mar 2010
First published
17 May 2010

Org. Biomol. Chem., 2010,8, 3045-3054

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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. de Vries and B. L. Feringa, Org. Biomol. Chem., 2010, 8, 3045 DOI: 10.1039/B924749A

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