Asymmetric autocatalysis: Triggered by chiral isotopomer arising from oxygen isotope substitution
Trigger happy: Chiral oxygen isotopomers of hydrobenzoin ([ 18O](R)-1 and [18O](S)-1) acted as chiral triggers to induce the enantioselective addition of iPr2Zn to pyrimidine-5-carbaldehyde. An extremely small chiral influence arising from the presence of the oxygen isotope (18O) is amplified through asymmetric autocatalysis to enantioenrich the 5-pyrimidyl alkanol product.