Chemoselective SN2′ Allylations of Detrifluoroacetylatively In Situ Generated 3-Fluoroindolin-2-one-Derived Tertiary Enolates with Morita-Baylis-Hillman Carbonates

The first example of the S(N)2' reaction type of the detrifluoroacetylatively in situ generated tertiary fluoroenolates in the uncatalyzed reactions with Morita-Baylis-Hillman derivatives has been described. The S(N)2' substitution takes place in a highly chemoselective manner as no corresponding S(N)2 products were observed in the reaction mixtures. Due to the excellent stereochemical outcome, the reactions seem to have an apparent synthetic value for the preparation of structurally new fluorinated oxindoles.