Optical Resolution of Racemic α‐Hydroxycarboxylic Acids on a Dynamic Chiral Stationary Phase Derived from (S)‐Leucinol by Ligand Exchange Chromatography.

Synthesis and Application of C2 and C3 Symmetric (R)‐Phenylglycinol‐Derived Chiral Stationary Phases

“…These aminoalcohol‐derived CSPs have some merits compared with amino acid‐derived CSPs in short and simple synthetic processes. Among the various amino‐alcohol‐derived CSPs, (R)‐phenylglycinol‐ and (S)‐leucinol‐derived CSPs showed better results in the resolution of many chiral samples . A CSP derived from a synthetic amino alcohol, (S)‐1‐anilino‐3‐propyl‐2‐propanol, has also been reported …”

“…Among the various amino-alcohol-derived CSPs, (R)-phenylglycinol-and (S)-leucinol-derived CSPs showed better results in the resolution of many chiral samples. [13][14][15][16] A CSP derived from a synthetic amino alcohol, (S)-1-anilino-3-propyl-2-propanol, has also been reported. 17 Some compounds with both chirality and a symmetric element have been used as chiral catalysts in the Diels-Alder reaction, 18,19 ethylation of benzaldehyde, 20 and addition reaction of β-ketoester.…”

Development of an improved ligand exchange chiral stationary phase based on leucinol for the resolution of proton pump inhibitors

“…Proline, hydroxyproline or other amino acids have been successfully utilized as chiral selectors for the preparation of ligand exchange CSPs [4][5][6][7]. Amino alcohol derivatives such as (S)-leucinol derivative, sodium N-[(S)-1-hydroxymethyl-3-methylbutyl]-Nundecylaminoacetate, and (R)-phenylglycinol derivative, sodium N-[(R)-2-hydroxy-1-phenylethyl]-N-undecylaminoacetate, covalently bonded to silica gel [10,11] or dynamically coated on octadecylsilica gel [12] were also quite successful as ligand exchange CSPs for the resolution of ␣-and ␤-amino acids and ␣-hydroxycarboxylic acids [10][11][12][13][14][15][16][17]. Especially, a CSP (CSP 1, Fig.…”

Amino alcohol‐derived chiral stationary phases

“…65,66 Since then, the use of amino alcohols, including the (1S,2R)-norephedrine, has been reported for the preparation of CSPs to perform the CLEC. [69][70][71][72][73][74][75][76][77][78][79][80][81] The α-amino alcohol-based CSPs have been frequently reported in chiral separation without the use of the ligand exchange mode. 67,[82][83][84][85][86][87][88][89] First, Pirkle-type π-acidic CSP prepared by our group, based on an α-amino alcohol, was an (R)-phenylglycinol 3,5-dinitrobenzoyl derived CSP.…”

“…Studies using amino alcohols to prepare CSPs for chiral separations have been reported by Yuki et al, 70,71 Mamiany et al, 105 Hyun et al, 65,66,[72][73][74][75][76][77][78][79] and Ryoo et al 67,[73][74][75][76][77][82][83][84][85][86][87][88][89] The development of ligand-exchange CSPs based on amino alcohols and their derivatives was reviewed in 2018 based on the work of Hyun. 72 To the best of our knowledge, there have been no further studies on amino alcohol-based CSPs other than those mentioned above to this date.…”