Generation of Chirality by Crystallization of Achiral Organic Compounds and Asymmetric Autocatalysis Induced by Chiral Organic Crystals

Abstract

Many achiral organic compounds can crystallize in chiral form to generate the chirality in solid-state. We have investigated the asymmetric autocatalysis with amplification of enantiomeric excess using these crystal formed from achiral compounds as an origin of chirality. When the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde was performed in the presence of chiral crystal, 5-pyrimidyl alkanol was formed in highly enantioselective manner. The absolute configuration of resulting pyrimidyl alkanol was well controlled by the crystal chirality of achiral organic compounds.