Catalytic enantioselective Michael addition reactions between in situ detrifluoroacetylatively generated 3-fluorooxindole-derived enolates and 1-(1-(phenylsulfonyl)vinylsulfonyl)benzene

This research presents the first example of catalytic enantioselective Michael addition reactions between 1-(1-(phenylsulfonyl)vinylsulfonyl)benzene and detrifluoroacetylatively in situ generated 3-fluorooxindole-derived enolates. The optimal catalyst includes Cu(OTf)(2) and (1S,2S)-1,2-diphenylethane-1,2-diamine featuring NHR functionalities. The reactions are conducted in THE at -20 degrees C using DIPEA as a base. The additions show reasonably high degree of structural generality and, therefore, synthetic value for preparation of a new family of compounds possessing pharmacophoric 3-fluorooxindole moiety, solofeaturing quaternary C-F stereogenic center.