Asymmetric autocatalysis with amplification of enantiomeric excess utilizing chiral crystals of achiral o-terphenyls as chiral triggers

Chiral crystals composed of achiral hydrocarbon o-terphenyl and its dimethoxy derivative, 4′,5′-dimethoxy-o-terphenyl have been successfully employed as chiral triggers in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde. In conjunction with asymmetric autocatalysis, that is, the Soai reaction, 5-pyrimidyl alkanol with remarkably enhanced enantiomeric excess (up to >99.5% ee) has been synthesized. The resulting 5-pyrimidyl alkanols exhibit the absolute configurations corresponding to those of the enantiomorphic o-terphenyls. These current findings highlight the capability of asymmetric autocatalysis to establish a connection between the crystal chirality of achiral hydrocarbon, such as o-terphenyls and the highly enantioenriched organic compounds.