Highly Enantioselective Allylic Amination by Cinchona Alkaloids

Significance

This report describes the first enantioselective organocatalytic allylic amination where the allylic C-H bond is activated by a chiral base. Dimeric cinchona alkaloids previously established as chiral organocatalysts by Deng et al. were shown to be effective catalysts for the amination reaction at low temperature. High yields (80-90%) and excellent ee’s (90-99%) were obtained from various alkylidene cyanoacetates. Interestingly, the enantioselectivity is not affected by the nature of the ester group or by the solvent polarity.