Role of Asymmetric Autocatalysis in the Elucidation of Origins of Homochirality of Organic Compounds

DOI Web Site 被引用文献7件 参考文献132件
  • Kenso Soai
    Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
  • Tsuneomi Kawasaki
    Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
  • Arimasa Matsumoto
    Department of Chemistry, Biology and Environmental Science, Nara Women’s University, Kita-Uoya Nishi-machi, Nara 630-8506, Japan

書誌事項

公開日
2019-05-20
資源種別
journal article
権利情報
  • https://creativecommons.org/licenses/by/4.0/
DOI
  • 10.3390/sym11050694
公開者
MDPI AG

説明

<jats:p>Pyrimidyl alkanol and related compounds were found to be asymmetric autocatalysts in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde and related aldehydes. In the asymmetric autocatalysis with amplification of enantiomeric excess (ee), the very low ee (ca. 0.00005%) of 2-alkynyl-5-pyrimidyl alkanol was significantly amplified to >99.5% ee with an increase in the amount. By using asymmetric autocatalysis with amplification of ee, several origins of homochirality have been examined. Circularly polarized light, chiral quartz, and chiral crystals formed from achiral organic compounds such as glycine and carbon (13C/12C), nitrogen (15N/14N), oxygen (18O/16O), and hydrogen (D/H) chiral isotopomers were found to act as the origin of chirality in asymmetric autocatalysis. And the spontaneous absolute asymmetric synthesis was also realized without the intervention of any chiral factor.</jats:p>

収録刊行物

  • Symmetry

    Symmetry 11 (5), 694-, 2019-05-20

    MDPI AG

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