Optical resolution and epimerization of fluorosilane having an optically active amino group: A new, convenient access to optically active silicon compounds
A. Kawachi et al., Optical resolution and epimerization of fluorosilane having an optically active amino group: A new, convenient access to optically active silicon compounds, ORGANOMETAL, 18(22), 1999, pp. 4530-4533
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).