Chiral separation of substituted phenylalanine analogues using chiral palladium phosphine complexes with enantioselective liquid-liquid extraction.
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. (31)P 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.
Verkuijl
Bastiaan J V
BJ
Laboratories for Organic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Schuur
Boelo
B
Minnaard
Adriaan J
AJ
de Vries
Johannes G
JG
Feringa
Ben L
BL
D005591:Chemical Fractionation / Q000379:methods*; D007700:Kinetics; D008024:Ligands; D009281:Naphthalenes / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification*; D010720:Phosphines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013696:Temperature
C406943:BINAP, 2-naphthol; D008024:Ligands; D009281:Naphthalenes; D009942:Organometallic Compounds; D010720:Phosphines; D012997:Solvents; D010649:Phenylalanine; D010165:Palladium; C044646:phosphine