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

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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-02, Vol.364 (4), p.732-737
Main Authors: Zhou, Xiao‐Le, Yeung, Chi‐Tung, Kwok Chan, Wesley Ting, Law, Ga‐Lai
Format: Article
Language:English
Subjects:
bidirectional
C(sp3)−H functionalization
Hydrogen bonds
Lewis acid
Lewis acid catalysis
Reaction mechanisms
Sc(OTf)3
Stereoselectivity
trans/cis diastereoselectivity
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101187