Asymmetric transformation of (RS)-2-phenylglycine via formation of salt with(1S)-10-camphorsulfonic acid.

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概要

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• An asymmetric transformation of (<I>RS</I>)-2-phenylglycine [(<I>RS</I>)-Phg] was carried out via formation of a salt with (1<I>S</I>)-10-camphorsulfonic acid [(<I>S</I>)-CS] in acetic acid, propanoic acid, or butanoic acid by heating at 100 °C without using any catalysts such as aldehydes. The rate of epimerization of a more soluble salt of (<I>S</I>)-Phg with (<I>S</I>)-CS was estimated to be lowest in acetic acid and highest in butanoic acid. The asymmetric transformation in propanoic acid, however, was achieved successfully to give the salt of (<I>R</I>)-Phg with (<I>S</I>)-CS with 100% optical purity in 82% yield. Optically pure (<I>R</I>)-Phg was obtained from the salt in 80% yield based on the (<I>RS</I>)-Phg used as the starting material.

• 公益社団法人 日本化学会の論文

著者

• Sakata Shinji

  Faculty Of Pharmaceutical Sciences Teikyo University

• KUROKAWA Hidemoto

  Faculty of Engineering and High Technology Research Center, Kansai University

• Shiraiwa Tadashi

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Fujishima Keiko

  Faculty of Engineering, Kansai University

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