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).
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry