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

1
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
2
Department of Chemistry, Biology and Environmental Science, Nara Women’s University, Kita-Uoya Nishi-machi, Nara 630-8506, Japan
*
Author to whom correspondence should be addressed.
Symmetry 2019, 11(5), 694; https://doi.org/10.3390/sym11050694
Received: 29 April 2019 / Revised: 15 May 2019 / Accepted: 16 May 2019 / Published: 20 May 2019
(This article belongs to the Special Issue Possible Scenarios for Homochirality on Earth)
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. View Full-Text
Keywords: asymmetric autocatalysis; homochirality; chirality; asymmetric synthesis; Soai reaction asymmetric autocatalysis; homochirality; chirality; asymmetric synthesis; Soai reaction
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Soai, K.; Kawasaki, T.; Matsumoto, A. Role of Asymmetric Autocatalysis in the Elucidation of Origins of Homochirality of Organic Compounds. Symmetry 2019, 11, 694.

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