Enantioselective Synthesis Induced by the Helical Molecular Arrangement in the Chiral Crystal of Achiral Tris(2-hydroxyethyl) 1,3,5-Benzenetricarboxylate in Conjunction with Asymmetric Autocatalysis

Abstract

Abstract 5-Pyrimidyl alkanol with an enantiomeric excess of up to >99.5% was formed using chiral crystals of achiral tris(2-hydroxyethyl) 1,3,5-benzenetricarboxylate as a chiral initiator. In the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde, the helicity of the molecular arrangement of achiral tricarboxylate in the crystalline state could be successfully used as a source of chirality to afford enantioenriched alkanol in conjunction with asymmetric autocatalysis with amplification of enantiomeric excess.