Organocatalytic Enantioselective Michael Reaction of Aminomaleimides with Nitroolefins Catalyzed by Takemoto’s Catalyst

Abstract

Known as electrophiles, maleimides are often used as acceptors in Michael additions to produce succinimides. However, reactions with maleimides as nucleophiles for enantioselective functionalization are only rarely performed. In this paper, a series of bifunctional Takemoto’s catalysts were used to organocatalyze the enantioselective Michael reaction of aminomaleimides with nitroolefins. The resulting products were obtained in good yields (76–86%) with up to 94% enantiomer excess (ee). The catalyst type and the substrate scope were broadened using this methodology.

Keywords

• Takemoto’s catalyst
• enantioselective
• Michael addition
• aminomaleimides
• nitroolefins