An asymmetric palladium and copper co-catalyzed Heck/Sonogashira reaction between
o-iodoacrylanilides and terminal alkynes to synthesize chiral oxindoles was developed.
In particular, a wide range of CF3-substituted o-iodoacrylanilides reacted with terminal
alkynes, affording the corresponding chiral oxindoles containing trifluoromethylated
quaternary stereogenic centers in high yields with excellent enantioselectivities
(94-98 % ee). This asymmetric Heck/Sonogashira reaction provides a general approach
to access oxindole derivatives containing quaternary stereogenic centers including
CF3-substituted ones.
