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. Stereospeci fic methylation and the deamination-fluorination of 2 give the enantiomeric ally pure (1-naphthyl)phenylmethylfluorosilane (1).