An enantioselective fluorination of 3functionalized oxindoles using electron-rich amino urea catalyst is described. Various 3-functionalized 3-fluoro-2-oxindoles were obtained in good yields and enantio-selectivity. The resulting enantioenriched 3-methylene nitrile 3-fluoro-2-oxindole product was found to inhibit indoleamine 2,3dioxygenase considerably.
Abstractα‐exo‐Methylene‐γ‐butyrolactones and α‐exo‐methylene‐δ‐valerolactones constitute an important group of natural and bioactive products. An enantioselective halolactonization of dienoic acids using (DHQD)2PHAL catalyst is described. Various halogenated α‐exo‐methylene‐γ‐butyrolactones and α‐exo‐methylene‐δ‐valerolactones were obtained in high yields and enantioselectivities. The resulting enantioenriched halogenated α‐exo‐methylene‐lactones were found to exhibit significant tumor‐inhibiting activities.magnified image
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