| Research Abstract |
We have mainly studied on optical resolutions with crystallization methods which are classified as preferential crystallizations and diastereomeric crystallizations. Using a preferential crystallization method, the salt of p-toluenesulfonic acid and 3-methyl-2-phenyl-1-butylamine which was useful for an optical resolution of ibuprofen was resolved. Analogously, the salt of 1-aminoindan or 1-aminotetralin and phenylacetic acid was successfully resolved. It was also clarified that 2-oxo-4,5-diphenyl-1,3-oxazolidine derived from erythro-2-amino-1,2-diphenylethanol was resolved with the preferential crystallization method. Concerning the diastereomeric crystallization methods, we developed 2-aryl-3-methylbutylamines and erythro-2-amino-1,2-diphenylethanol series as basic optical resolving agents. Thus, their preparation methods and utilities were established. On the other hand, 2-phenylpropanesulfonic acid and 2- (p-isobutylphenyl) propanesulfonic acid were derived from 2-phenylpropanoic a
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cid or 2- (p-isobutylphenyl) propanoic acid.In this way the strong acidic chiral sulfonic acids were successfully developed. Using these optical resolving agents, alpha-amino-epsilon-caprolactam, proline, pipecolic acid, tert-leucine, tryptophan, dihydrojasmonic acid, jasminlactone, tuberolactone, delta-decalactone and chroman-2-carboxylic acid were effectively resolved.
New ferroelectric liquid crystals (FLCs) derived from optically active fluorinated alkanol were synthesized, and a relationship between rotational viscosity and the fluorinated position of FLCs was clarified. Using optically active 1,1,1-trifluoro-2-alkanols resolved by trans-2- (benzamido) cyclohexane carboxylic acid, many FLCs and antiferroelectric liquid crystals were synthesized. Novel FLCs having a semi-perfluorinated terminal chain were synthesized, and a relationship between fluorination extent and mesophases properties was elucidated. Many liquid crystals derived from newly designed optically active compound, 4,4,4-trifluoro-3- (4-methoxyphenyl) butanoic acid, were synthesized. Thus, novel AFLCs without any carbonyl moiety in the molecule were found. Some chiral nematic materials having fluorinated asymmetric frame were synthesized, and a relationship between their structures and a helical twisting power were evaluated.
An optically active spiropyran with trans-2- (benzamido) cyclohexane carboxylate moiety was synthesized, and its photochromic properties were analyzed by X-ray structural analysis and NMR spectroscopy. Some novel spiropyran metal complexes were synthesized, and their molecular structures were determined by X-ray analysis. Less
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