Axially Chiral Dicarboxylic Acid Catalyzed Formal Alkenylations of Imines

Significance

A novel enantioselective formal ­alkenylation of imines using axially chiral dicarboxylic acid 1 as a catalyst has been reported. In this reaction, the imine protecting group was crucial to obtain high enantioselectivities. Racemic products were observed with the Boc instead of the benzoyl group. The authors demonstrated the synthetic use of this reaction by converting the aza-enamine products into β-substituted γ-amino nitrile compounds in good yields and high enantioselectivities. This approach can be used for the synthesis of γ-amino acids.