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Tetrahedron v.74 no.16, 2018년, pp.1973 - 1990   SCI SCIE SCOPUS
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Asymmetric autocatalysis of pyrimidyl alkanol and related compounds. Self-replication, amplification of chirality and implication for the origin of biological enantioenriched chirality

Soai, Kenso (Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan ) ; Kawasaki, Tsuneomi (Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan ) ; Matsumoto, Arimasa (Faculty of Science, Nara Women's University, Kita-Uoya Nishi-machi, Nara, 630-8506 Japan ) ;
  • 초록  

    Abstract We discovered asymmetric autocatalysis in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde, where the product 5-pyrimidyl alkanol acts as a highly efficient asymmetric autocatalyst to afford more of itself (Soai reaction). Asymmetric autocatalysis proceeded quantitatively (>99% yield), affording itself as a near enantiomerically pure (>99.5% ee) product. An extremely low enantiomeric excess ( ca . 0.00005% ee) can automultiply during three rounds of consecutive asymmetric autocatalysis to >99.5% ee by asymmetric amplification. Circularly polarized light, and inorganic and organic crystals, act as the origin of chirality to trigger asymmetric autocatalysis. Asymmetric autocatalysis has enormous power to recognize and amplify the chirality of hydrogen, carbon, oxygen, and nitrogen isotopomers. Moreover, absolute asymmetric synthesis, i.e. , the formation of enantioenriched compounds without the intervention of any chiral factor, is realized by asymmetric autocatalysis. By using designed molecules based on 5-pyrimidyl alkanol, the intramolecular asymmetric control, self-replication, and improvement of chiral multifunctionalized large molecules has been developed by applying asymmetric autocatalysis. Graphical abstract [DISPLAY OMISSION]


  • 주제어

    Asymmetric autocatalysis .   Amplification of ee .   Pyrimidyl alkanol .   Origin of homochirality .   Chiral crystallization .   Remote intramolecular asymmetric control .   Isotope chirality .   Self-replication.  

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