Enantioselective Catalyzed Synthesis of Amino Derivatives Using Electrophilic Open-Chain N-Activated Ketimines

N-Activated ketimines are characterized by the presence of acyl, sulfonyl, and phosphinoyl groups linked to the nitrogen atom of the azomethine system. These electron-withdrawing groups enhance the electrophilic character of the imino moiety allowing the addition of even weak nucleophilic reagents. The presence of the oxygen atoms in these activating groups with its coordinating and Lewis or Bronsted properties is of paramount importance in asymmetric catalyzed reactions. This review collects the results that have appeared in the literature during the last two decades on the utilization of open-chain N-activated ketimines for the synthesis of optically active alpha-disubstituted and alpha-trisubstituted amino derivatives including nitrogen-containing heterocyclic compounds.

Automated summary

N-Activated ketimines are characterized by electron-withdrawing groups linked to the nitrogen atom, enhancing the electrophilic character and allowing addition reactions with weak nucleophiles. The presence of oxygen atoms in these groups is crucial for asymmetric catalytic reactions. This review summarizes the literature on the synthesis of optically active alpha-substituted amino derivatives using open-chain N-activated ketimines.