Iridium-Catalyzed Regio- and Diastereoselective Synthesis of C-Substituted Piperazines.

ABSTRACT: Piperazine rings are essential motifs frequently found in commercial drugs. However, synthetic methodologies are mainly limited to N-substituted piperazines, preventing structural diversity. Disclosed herein is a straightforward catalytic method for the synthesis of complex C-substituted piperazines based on an uncommon head-to-head coupling of easily prepared imines. This 100% atom-economic process allows the selective formation of a sole diastereoisomer, a broad substrate scope, and a good functional group tolerance employing a bench-stable iridium catalyst under mild reaction conditions. Key to the success is the addition of N-oxides to the reaction mixture, as they notably enhance the catalytic activity and selectivity.

SUBMITTER: Tarifa L 

PROVIDER: S-EPMC9990149 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature