Abstract
AbstractWe have discovered an asymmetric autocatalysis in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde, where the product, 5-pyrimidyl alkanol, acts as highly efficient asymmetric autocatalyst. Asymmetric autocatalysis proceeded quantitatively (>99%), affording itself as a near enantiomerically pure (>99.5% ee) product. An extremely low enantiomeric excess (ca. 0.00005% ee) can automultiply during three consecutive asymmetric autocatalysis to >99.5% ee. Circularly polarized light, quartz, chiral organic crystals, and statistical fluctuation of ee in racemate, which are considered a possible candidate for the origin of chirality, act as the chiral source in asymmetric autocatalysis. Asymmetric autocatalysis has the enormous power to recognize the isotope chirality arising from the small difference between carbon (carbon-13/carbon-12) and hydrogen (D/H) isotopes.KeywordsAmplification of eeAsymmetric autocatalysisAutomultiplicationChiral discriminationCircularly polarized lightQuartzIsotope chiralityOrigin of chiralityPyrimidyl alkanolSpontaneous absolute asymmetric synthesis
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