| Abstract: | A novel strategy was developed for the asymmetric synthesis of fluorinated vicinal diamines.Deprotonation of N-(diphenylmethylene)-benzylamines under base,followed by asymmetric nucleophilic addition to N-tert-butanesulfinylfluoroacetaldimines,a pair of diastereomeric isomers were afforded.The diastereomeric isomers can be easily separated from each other by silica gel column chromatography.The absolute steric configuration of two isomers was confirmed by single crystal X-ray diffraction analyses.The proposed mechanism revealed that the configuration of the carbon next to tert-butanesulfinyl was well controlled to be R by the chiral auxiliary. |
