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Total Spontaneous Resolution by Deracemization of Isoindolinones

Authors

  • Fumitoshi Yagishita,

    1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)
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  • Hiroki Ishikawa,

    1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)
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  • Tatsuo Onuki,

    1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)
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  • Shoko Hachiya,

    1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)
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  • Prof. Takashi Mino,

    1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)
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  • Prof. Masami Sakamoto

    Corresponding author
    1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)
    • Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)
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  • This work was supported by Grants-in-Aid for Scientific Research (Nos. 21350024, 22655012) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of the Japanese Government.

Abstract

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Separated: 3-Hydroxy-3-phenylisoindolin-1-ones have been resolved by dynamic preferential crystallization. The compounds were effectively racemized through ring-opening and ring-closing reactions via achiral intermediates under basic conditions. Crystallization from a toluene solution containing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with stirring and evaporation of the solvent gave optically active crystals quantitatively with high ee values.

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