• Bulletin of the Korean Chemical Society
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• v.35 no.7
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• pp.1989-1995
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• 2014

The small library of new enantiomerically pure (S,S)-diamino alcohols 1 and their hydroxyldiamide precursors 2 were conveniently synthesized on a gram scale from inexpensive and commercially chiral pool amino acids. The catalytic and induced asymmetric effects of the chiral ligands 1 in the asymmetric allylic oxidation of cycloolefins were investigated.

• KSBB Journal
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• v.26 no.4
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• pp.323-327
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• 2011

The convenient derivatization method of chiral amino alcohols as 9-anthraldimine Schiff base derivatives for chiral resolution was developed and the liquid chromatographic enantiomer separation of chiral amino alcohols as 9-anthraldimine derivatives was investigated on several coated and covalently bonded polysaccharide-derived chiral stationary phases (CSPs). In general, the performance of Chiralcel OD-H (or Chiralcel OD) (${\alpha}$ = 1.24-2.89), the coated CSP derived from cellulose derivative was superior to the other CSPs for resolution of 9-anthraldimine derivatives of several amino alcohols. The results of enantioseparation depending on the structure of 9-anthraldimine analytes like the steric bulky group and the polar moiety etc were discussed. The analytical method was applied to measure the enantiomeric purity of commercially available chiral amino alcohols. It is expected that the convenient analytical method will be very efficient for determination of enantiomeric purity of amino alcohols as 9-anthraldimine Schiff base derivatives with strong UV absorption.

• Bulletin of the Korean Chemical Society
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• v.24 no.11
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• pp.1695-1698
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• 2003

• Bulletin of the Korean Chemical Society
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• v.25 no.9
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• pp.1385-1391
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• 2004

A general route for the synthesis of optically active unhindered aliphatic alcohols, where the steric demands between two alkyl groups adjacent to the carbinol are similar, with high enantiomeric purity has been developed by sulfoxifation of chiral ${\beta}$-hydroxy sulfides, followed by alkylation and desulfurization.

• Advances in materials Research
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• v.2 no.1
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• pp.51-64
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• 2013

Enantioselective macromer of trimesic acid was prepared using S(-) menthol with trimesoyl chloride on polyimide (PI) ultrafiltration membrane. The chemical composition of macromer as well as polyimide ultrafiltration membrane was determined by ATR-FTIR Spectroscopy. The optical resolution of chiral alcohols was performed in pressure driven process. The effect of monomer solutions concentration, effect of air-drying time of S(-) menthol solution, effect of reaction time, effect of operating pressure, effect of feed concentration of racemate on the performance of macromer was studied. The synthesised material exhibits separation of chiral alcohols (menthol ~23% and sobrelol ~21%).

• Bulletin of the Korean Chemical Society
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• v.31 no.4
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• pp.869-873
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• 2010

A series of novel chiral tert-amino alcohols 4a-h derived from enantiomerically pure phenylalanine were synthesized efficiently and used as chiral ligands in the catalytic enantioselective ethylation of aldehydes with diethylzinc (diethylzinc-to-aldehyde addition). The use of 10 mol % of the amino alcohols led to the corresponding sec-alcohols with excellent enantioselectivities (up to 100% ee) and high yields.

• Journal of Photoscience
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• v.6 no.4
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• pp.165-170
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• 1999

Asymmetric recognition of chiral alcohol by fluorenone derivatives with chiral substituents through intermolecular hydrogen bonding interaction in the singlet excited state was attempted. 1-((1S, 2R, 5S)-(+)-Menthyloxycarbonyl)aminofluoren-9-one (1-MAF) and 1-((1S, 2R, 5S)-(+)-menthyloxycarbonyl)oxyfluoren-9-one (1-MOF) were synthesized and their photophysical behaviors were characterized by the measurement of absorption and fluorescence spectra, as well as the quantum yield and the lifetime of fluorescence. The excited singlet states of 1-MAF and 1-MOF were revealed to have characteristics similar to those of fluorenone, though the intramolecular CT nature was fairly suppressed as compared with 3- and 4-substituted aminofluorenones. Fluorescences of 1-MAF and 1-MOF in acetonitrile were quenched by the addition of alcohols. Differences in fluorescence quenching efficiency were hardly observe for rather small chiral alcohols such as (R)-(-)- or (S)-(+)-2-butanol, while bulky alcohols such as menthol and isopinocampheol showed chiral recognition effects in their fluorescence quenching of 1-MAF in either acetonitrile or butyronitrile.

• Bulletin of the Korean Chemical Society
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• v.17 no.8
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• pp.673-674
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• 1996

• Bulletin of the Korean Chemical Society
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• v.32 no.4
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• pp.1263-1267
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• 2011

Novel binol-based uryl and guanidinium receptors having higher ring conjugation at the periphery of the hydrogen bonding donor sites have been synthesized and utilized to study the enantioselective recognition of 1,2-aminoalcohols and chirality conversion of natural amino acids via imine bond formation. There is a remarkable decrease in the stereoselectivites as the conjugation increases at the periphery of hydrogen bonding donor sites. The guanidinium-based receptors show more selectivity towards the amino alcohol than that of the uryl based ones due to its charge reinforced hydrogen bonds. The conversion efficiency of L-amino acids to Damino acids by the uryl-based receptors is higher than that of the guanidinium-based ones.

• Bulletin of the Korean Chemical Society
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• v.30 no.12
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• pp.2938-2942
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• 2009

New receptors 1-3 that bind stereoselectively amino alcohols and convert chirality of amino acidsvia imine bond formation were synthesized. The receptors have uryl (1), thiouryl (2) and guanidinium (3) groups all with additional phenylcarbonyl motifs, which are effective hydrogen bonding donors and play a key role in the stereoselective recognitions. The stereoselectivities were measured from the integration of $^1HNMR$ peaks. Compound 1 and 2 showed the stereoselectivities for the imine formation with amino alcohols ($K_R/K_S$) in the range of 2${\sim}$4, and compound 3 in the range of 4${\sim}$8. Chirality conversion efficienciesof 1-3 for amino acids, i.e. D/L ratio at equilibrium, are in the range of 1.5${\sim}$5.6, showing a little higher efficiency with 3. The additional phenylcarbonyl motifs in 1-3 were revealed not to contribute to significant enhancement of the selectivities.