Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins

Abstract

The investigation of a Lewis base catalyzed asymmetric allylic amination of Morita–Baylis–Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high yields (up to 97%).

Keywords

• allylic amination
• asymmetric organocatalysis
• Morita–Baylis–Hillman carbonates
• 2-oxindoles
• quaternary chiral center