Asymmetric Autocatalysis: The Soai Reaction
Chapter 2: Asymmetric Autocatalysis Initiated by Enantioenriched Chiral Organic Compounds: The Link Between Circularly Polarized Light and Nearly Enantiopure Organic Compounds
Published:28 Oct 2022
Special Collection: 2022 ebook collectionSeries: Catalysis Series
Tsuneomi Kawasaki, Arimasa Matsumoto, Kenso Soai, 2022. "Asymmetric Autocatalysis Initiated by Enantioenriched Chiral Organic Compounds: The Link Between Circularly Polarized Light and Nearly Enantiopure Organic Compounds", Asymmetric Autocatalysis: The Soai Reaction, Kenso Soai, Tsuneomi Kawasaki, Arimasa Matsumoto
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Various enantioenriched chiral compounds act as chiral initiators for asymmetric autocatalysis without sufficient enantiomeric excess (ee) and significant chiral directing power. Through the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc in the presence of enantioenriched chiral compound, a highly enantioenriched 5-pyrimidyl alkanol can be synthesized with a corresponding absolute configuration to the handedness of the chiral compound thanks to the significant amplification of ee by asymmetric autocatalysis. Asymmetric autocatalysis is a powerful sensor for recognizing the chiral factor of target materials, thereby discriminating the hidden cryptochirality such as seen in chiral saturated quaternary hydrocarbons and isotactic polystyrene, a highly enantioenriched 5-pyrimidyl alkanol with an easily analyzable chiral carbon center can be synthesized as a reaction outcome. Moreover, chiral compounds whose enantioimbalance is induced by the irradiation of circularly polarized light (CPL) can act as a chiral initiator for the asymmetric autocatalysis of 5-pyrimidyl alkanol. Thus, CPL is linked with an enantiomerically pure organic compound, mediated by asymmetric autocatalysis with amplification of ee. Therefore, CPL can be an origin of homochirality of organic compounds in conjunction with asymmetric autocatalysis.