Nucleophilic aromatic substitution 3- nitroaniline

Chiral Brpnsted acids have also been shown to effectively catalyze the Mannich reaction between aldehydes, anilines, and enecarbamates [100]. Here, the application of enecarba-mates as nucleophilic species instead of ketones gives access to enantioenriched 1,3-diamines after subsequent reduction in situ with sodium cyanoborohydride. The potential of this approach was demonstrated by reacting various aromatic or aliphatic aldehydes and substituted enecarbamates with para-nitroaniline in the presence of the chiral phosphoric acid catalyst 150 (Scheme 11.34). 

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