The Soai reaction and its implications with the life's characteristic features of self-replication and homochirality
2022
Soai, Kenso
Asymmetric autocatalysis is a reaction in which chiral product acts as a chiral catalyst for its own production. The process is a self-replication of chiral molecules with amplification of enantiomeric excess (ee). In the Soai reaction, (S)-pyrimidyl alkanol with extremely low ee acts as asymmetric autocatalyst in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde to afford more of the (S)-pyrimidyl alkanol of the same structure with significantly enhanced greater than 99.5% ee. The Soai reaction is capable of absolute asymmetric synthesis. Thus, the reaction between achiral diisopropylzinc and pyrimidine-5-carbaldehyde without the intervention of any chiral factor affords enantioenriched pyrimidyl alkanol with stochastic distribution. The proposed origins of homochirality such as quartz and circularly polarized light are correlated to highly enantioenriched compound by using the Soai reaction. The implications of the Soai reaction is described in the selected life's characteristic features of self-replication and homochirality.
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