Diastereoselective Bidirectional C(sp³)−H Bond Functionalization of Piperazine Compounds

Abstract

A highly diastereoselective bidirectional C(sp3)−H bond functionalization of piperazine compounds, triggered by a Lewis acid catalyzed sequential hydride shift/cyclization process, is reported. Catalysts and ligands are key factors that control the diastereoselectivity of the reaction. The reaction affords the product with good yield and high diastereoselectivity. Detailed investigation of the reaction mechanism reveals that the energy barrier between the cis products and trans products results in the diastereoselectivity of the reaction. The trans products, which have higher energy and which are generated from the cis products, act as intermediate products.