A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions

Nitro-charged activation: An organocatalytic enantioselective conjugate addition of aryl methyl nucleophiles to enals has been developed to produce ubiquitous chiral benzylic building blocks (see scheme; TES=triethylsilyl). Taking advantage of the strongly electron-withdrawing nature of nitro groups, which can be conveniently transformed into other functionalities, this functionality was incorporated into aromatic systems as a temporary activating group.