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Chiral compounds have been mainly used in the pharmaceutical industry. Drugs which have asymmetric carbon(s) in their structure are usually developed as a single stereoisomer (FDA announcement, Chirality 1992, 4, 338.). Therefore, the demand of the chiral building blocks is increasing with time.
We have been developing synthetic methodologies for chiral building blocks and their derivatives at the commercial scale. The optically active compounds used in our projects are commercially available ones as well as DAISO's own original C3 and C4 chiral chemicals. And also, at DAISO, we are now developing the optical resolution of racemic derivatives of α-amino acid or hydroxycarboxylic acids, and desymmetrization of meso-carboxylic anhydride compounds in the presence of catalysts derived from cinchona alkaloid . |
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| We obtained a license of Jacobsen's hydrolytic kinetic resolution technology for the manufacture and sale of chiral epichlorohydrin and chiral 3-chloro-1,2-propanediol from Rhodia (former ChiRex, Inc.) (June, 2000). This technology that is shown in eq.1 is developed by Professor Jacobsen of Harvard University in 1997 (E. N. Jacobsen, et al., Science, 1997, 277, 936.). |
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| In July 2001, we received an exclusive license for a kinetic resolution technology using chiral amine, Cincona alkaloids, as a catalyst to prepare the chiral a-amino acids and chiral hydroxycarboxylic acids invented by Professor Li Deng of Brandeis University, USA. As this technology can be applied with no limitation, a wide range of chiral α-amino acids and chiral hydroxycarboxylic acids can be provided. The catalysts is repeatedly usable after the isolation process that is a simple acid-base extraction |
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| In March 2003, we also received an exclusive worldwide license for the desymmetrization of mesomeric acid anhydrides using modified cinchona alkaloids as catalysts to prepare chiral hemi-esters invented by Professor Li Deng. ( L. Deng, et al., J. Am. Chem. Soc ., 2000, 122 , 9542). This desymmetrization technology has advantages that high yield (close to 100%) and high enantioselectivity are obtained. The catalyst is repeatedly usable after the isolation process that is a simple acid-base extraction.Chiral hemi-esters are easily converted to not only γ- and δ-hydroxy esters and γ- and d-lactones, but also γ- and d-amino acids and γ- and d-lactams. |
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