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.
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Kawasaki et al. (2005) studied this question.
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