Bulletin of the Chemical Society of Japan p. 109 - 113 (1989)
Update date:2022-08-11
Topics:
Shiraiwa, Tadashi
Kataoka, Kazuo
Sakata, Shinji
Kurokawa, Hidemoto
Either (R)- or (S)-cysteine ((R)- or (S)-Cys) was efficiently obtained from (RS)-Cys by the asymmetric transformation via formation of (RS)-thiazolidinecarboxylic acid ((RS)-THC) or (RS)-2,2-dimethyl-4-thiazolidinecarboxylic acid ((RS)-DMZ) and by using (2R,3R)- or (2S,3S)-tartaric acid ((R)- or (S)-TA), as a resolving agent, in acetic acid.The asymmetric transformation was carried out by combination of crystallization of less soluble salt of (S)-THC or -DMT with (R)-TA (or salt of (R)-THC or -DMT with (S)-TA) and epimerization of soluble diastereomeric salt.The (R)- and (S)-THCs from the less soluble salts gave approximately optically pure (R)- and (S)-Cys's, respectively, in 64percent yield.The asymmetric transformation via formation of (RS)-DMT was more succeefully achieved by adding 0.1 molar equivalent of salicylaldehyde; that is, hydrolysis of the obtained less soluble salt gave optically pure (R)- and (S)-Cys's, respectively, in 80percent yield based on the (RS)-Cys used as the starting material.
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