Asymmetric Autocatalysis Triggered by Chiral Crystals Formed from Achiral Compounds and Chiral Isotopomers |
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| Authors: | Tsuneomi Kawasaki Kenso Soai |
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| Affiliation: | Department of Applied Chemistry and Research Institute for Science and Technology, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan phone: +81 3 5228 8261 fax: +81 3 5261 4631, http://www.rs.kagu.tus.ac.jp/soai/ |
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| Abstract: | Asymmetric autocatalysis with amplification of enantiomeric excess is found in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde using pyrimidyl alkanol as an asymmetric autocatalyst. Asymmetric autocatalysis has been employed as a method for clarifying the origin of homochirality. Circularly polarized light, inorganic chiral crystals and statistical fluctuation of enantiomeric imbalance act as chiral initiators in asymmetric autocatalysis to afford highly enantioenriched products. We have investigated asymmetric autocatalysis using chiral crystals formed from achiral and racemic compounds as an origin of chirality. Absolute control of the crystal chirality of cytosine was achieved by the removal of crystal water. Enantioselective carbon-carbon bond formation at the enantiotopic crystal face of aldehydes was established using diisopropylzinc vapor. In addition, asymmetric autocatalysis triggered by chiral compounds arising from H, C and O isotope substitution has been achieved. |
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| Keywords: | asymmetric autocatalysis amplification of chirality origin of chirality homochirality chiral crystal isotope chirality |
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