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

Xiao Le Zhou, Chi Tung Yeung, Wesley Ting Kwok Chan, Ga Lai Law

Research output: Journal article publicationJournal articleAcademic researchpeer-review

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. (Figure presented.).

Original languageEnglish
Pages (from-to)732-737
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume364
Issue number4
DOIs
Publication statusPublished - 15 Feb 2022

Keywords

  • bidirectional
  • C(sp)−H functionalization
  • Lewis acid catalysis
  • Sc(OTf)
  • trans/cis diastereoselectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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