Synthesis of CuPF₆‐(S)‐BINAP loaded resin and its enantioselectivity toward phenylalanine enantiomers

Abstract

A type of resin-anchored CuPF -(S)-BINAP was synthesized and identified. The PS-CuPF -(S)-BINAP resin was used to adsorb the phenylalanine enantiomers. The results showed that the adsorption capacity of PS-CuPF -(S)-BINAP resin toward L-phenylalanine was higher than that of resin toward D-phenylalanine. PS-CuPF -(S)-BINAP resin exhibited good enantioselectivity toward L-phenylalanine and D-phenylalanine. The influence of phenylalanine concentration, pH, adsorption time, and temperature on the enantioselectivity of the resin were investigated. The results showed that the enantioselectivity of the resin increased with increasing the phenylalanine concentration, pH, and adsorption time, while it decreased with an increase in temperature. The causes for these influences are discussed. The highest enantioselectivity (α = 2.81) was obtained when the condition of phenylalanine concentration was 0.05 mmol/mL, pH was 8, adsorption time was 12 h, and temperature 5°C. The desorption test for removing D/L-phenylalanine on PS-CuPF -(S)-BINAP resin was also investigated. The desorption ratios of D-phenylalanine and L-phenylalanine at pH of 1 were 95.7% and 94.3%, respectively. This result indicated that the PS-CuPF -(S)-BINAP resin could be regenerated by shaking with an acidic solution. The reusability of the PS-CuPF -(S)-BINAP resin was also assessed and the resin exhibited considerable reusability.

Enantioselective liquid‐liquid extraction of 3‐chloro‐phenylglycine enantiomers using (S,S)‐DIOP as extractant

“…Recently, some diphosphine ligands used as chiral catalysts in asymmetric reactions have been proved to be effective chiral selectors in enantioselective liquid‐liquid extraction (ELLE) . For instance, ( S )‐BINAP‐metal, ( S )‐MeO‐BIPHEP‐metal, and ( S )‐SEGPHOS‐metal complexes have considerable abilities to separate amino acid and mandelic acid enantiomers . Since the chiral ligands in asymmetric reactions may be the good chiral selectors, it seemed interesting to further study this field with the goal of finding more ligands with favorable enantiomeric recognition and separation potency in ELLE.…”

“…[10][11][12][13][14][15] For instance, (S)-BINAP-metal, (S)-MeO-BIPHEP-metal, and (S)-SEGPHOS-metal complexes have considerable abilities to separate amino acid and mandelic acid enantiomers. [16][17][18] Since the chiral ligands in asymmetric reactions may be the good chiral selectors, it seemed interesting to further study this field with the goal of finding more ligands with favorable enantiomeric recognition and separation potency in ELLE.…”

Synthesis of citric acid-modified resins and their adsorption properties towards metal ions

“…This result revealed that citric acid was successfully anchored on resins. In addition, the absorption band in the vicinity of 678 cm −1 still existed in curves a1, which indicated that the –Cl groups were not fully substituted by citric acid during the reaction [ 17 , 18 ]. Curves b1, b2 and b3 in figure 3 are the FTIR spectra of PS-Cl, PS-OH and PS-O-CA, respectively.…”

Enantioselective liquid‐liquid extraction of DL‐mandelic acid using chiral diphosphine ligands as extractants

“…Recently, Verkuijl et al and Tang et al have reported that (S)-BINAP-metal complexes exhibited good abilities to separate amino acid enantiomers. 7,[16][17][18][19][20][21][22] And our precious works also revealed that (S)-MeO-BIPHEP and (S)-SEGPHOS have good abilities to recognize amino acid enantiomers. 23 These results indicated that chiral diphosphine ligands are excellent chiral extractants in enantioselective liquid-liquid extraction.…”

“…1,2 Tartaric acid, 3 crown ether, 4 cyclodextrin, 5 cinchona alkaloid, 6 and metal complex 7 are common chiral extractants that are widely used in enantioselective liquid-liquid extractions. 7,[16][17][18][19][20][21][22] And our precious works also revealed that (S)-MeO-BIPHEP and (S)-SEGPHOS have good abilities to recognize amino acid enantiomers. (S)-BINAP, (S)-MeO-BIPHEP, and (S)-SEGPHOS are important chiral catalysts that are widely used in asymmetric reactions.…”