Enantioselective synthesis induced by the helical molecular arrangement in the chiral crystal of achiral tris(2-hydroxyethy1 b) 1,3,5-benzenetricarboxylate in conjunction with asymmetric autocatalysis

Abstract

5-Pyrimidyl alkanol with an enantiomeric excess of up to >99.5% was formed using chiral crystals of achiral tris(2-hydroxyethy1 b) 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. © 2013 The Chemical Society of Japan.