Asymmetric Amplification Using Chiral Cocrystals Formed from Achiral Organic Molecules by Asymmetric Autocatalysis

Abstract

Enantioselective addition of diisopropylzinc to a pyrimidine-5-carbaldehyde was induced by chiral cocrystals of achiral two-component molecular crystals of tryptamine/para-chlorobenzoic acid (see scheme) and 3-indolepropionic acid/phenanthridine. This reaction, in conjunction with asymmetric autocatalysis, afforded a pyrimidyl alkanol in high enantiomeric excess.