930769-50-9Relevant academic research and scientific papers
HPLC enantioseparation on a homochiral MOF-silica composite as a novel chiral stationary phase
Tanaka, Koichi,Muraoka, Toshihide,Otubo, Yasuhiro,Takahashi, Hiroki,Ohnishi, Atsushi
, p. 21293 - 21301 (2016/03/08)
The last frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal-organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers of various kinds of racemic sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides. The experimental results showed excellent performances for enantioseparation, and highlighted that enantioseparation on homochiral MOF columns is practical.
Homochiral coordination polymers with nanotubular channels for enantioselective sorption of chiral guest molecules
Tanaka, Koichi,Kikumoto, Yuki,Hota, Naoki,Takahashi, Hiroki
supporting information, p. 880 - 883 (2014/03/21)
Two novel chiral coordination polymers were synthesized by treating C 2-symmetric 2,2′-dihydroxy- and 2,2′-dimethoxy-1, 1′-binaphthalene-3,3′-dicarboxylic acids with Cu2+, in which sorption of some chiral β-lactam compounds in the fr
A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams
Forro, Eniko,Paal, Tihamer,Tasnadi, Gabor,Fueloep, Ferenc
, p. 917 - 923 (2007/10/03)
A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).
