Optical Resolution and Epimerization of Fluorosilane Having an Optically Active Amino Group: A New, Convenient Access to Optically Active Silicon Compounds

The diastereomeric (amino)fluorosilane 2 is prepared from the prochiral (1-naphthyl)-phenyldifluorosilane 5 with optically active bis[(R)-1-phenylethyl]amine (3). The two isomers of 2 can be easily separated due to their large solubility difference in CH₃NO₂. In addition, 2 undergoes epimerization at the silicon atom in the presence of a catalytic amount of AgF. Stereospecific methylation and the deamination-fluorination of 2 give the enantiomerically pure (1-naphthyl)phenylmethylfluorosilane (1).