3,3-Disubstituted oxindole bearing a stereogenic 3-fluorinated carbon center is a privileged structural motif present in many bioactive molecules. The straightforward functionalization of 3-fluorooxindoles constitutes a powerful method for the synthesis...

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Ahighly selective TMG-catalyzed β-addition of (arylsulfonyl)fluoromethane derivatives to allenoates has been developed.Cyano, nitro, and ester-functionalized (arylsulfonyl)fluoromethanes are all suitable substrates, giving a series of structurally diverse β-addition products bearing a stereogenic fluorinated carbon center. A possible reaction pathway is also presented.

Both the α-amidoacrylate and 3-ylideneooxindole frameworks are important in medicinal chemistry because of their associated biological activities. We report a novel approach to accessing α-amidoacrylates containing a 3-ylideneoxindole motif through a novel cascade process involving condensation between 3-fluorooxindoles and α-iminoacetates followed by elimination of HF. This protocol has a broad substrate scope: Nalkyl-, N-aryl-, N-allyl-, N-propargyl 3-fluorooxindoles and 3fluorooxindoles with different substituents on the aromatic rings were all suitable for this reaction. A plausible reaction pathway is also presented.

We report a diastereoselective Mannich-type reaction of 3alkyloxindole with N-tert-butanesulfinyl imino ester. This method provides a concise route to α-amino acid derivatives bearing a 3-alkyloxindole structural motif. This protocol has the advantage of using readily accessible starting materials and is operationally simple. A plausible transition-state mode for the observed stereoselectivity is presented.