Asymmetric autocatalysis of a ferrocene-containing chiral compound with amplification of chirality

Chiral ferrocene-containing pyrimidyl alkanol can be efficiently synthesized via asymmetric autocatalysis as an enantiomerically pure product. Moreover, a remarkable positive nonlinear effect occurs during this autocatalytic reaction. Starting from a nearly racemic seed, it is thus possible to produce a larger amount of the same compound with high ee.

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(S)-1-(2-Ferrocenylethynyl-5-pyrimidyl)-2-methylpropan-1-olC20H20FeN2OEe >99%[α]D18=-18.0 (c 0.99, CHCl3)Source of chirality: asymmetric autocatalysisAbsolute configuration: S