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<p>The Mannich reaction represents one of the most fundamental reactions for the stereoselective synthesis of β-amino-carbonyl compounds and has been broadly applied in organic synthesis. In contrast, the homologue of the Mannich reaction, the so-called the homo-Mannich reaction, which generates the homologated γ-amino-carbonyl products, remains largely underexplored despite its potential for diverse applications. We show here a copper-catalysed homo-Mannich reaction of cyclopropanols with in situ-formed imines, furnishing a variety of chiral 2,6-disubstituted piperidines in good yields with high diastereoselectivities. Critical is the use of a diketiminate-complexed copper as the catalyst, which allows this reaction to proceed efficiently under mild conditions in an air atmosphere. Using this method as the key reaction, we achieved total synthesis of four alkaloids. This study not only expands the application range of cyclopropanol as a homoenolate equivalent for the Mannich reaction, but also inspires utilization of diketiminate ligands in metal catalysis.</p><p></p>

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Copper-catalysed homo-Mannich reaction of cyclopropanol for chiral piperidine synthesis

  • 期刊论文

  • 发表日期：

    2025年10月24日

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  • Yankun Zhao,
  • Wenxuan Lin,
  • Yulian Zhang,
  • Guangcheng Pu,
  • Zhuoyuan Jian,
  • Hongya Yan,
  • Ling He,
  • Chengyang Wang,
  • Qiuyuan Tan,
  • Yu Lan,
  • Min Zhang

摘要

The Mannich reaction represents one of the most fundamental reactions for the stereoselective synthesis of β-amino-carbonyl compounds and has been broadly applied in organic synthesis. In contrast, the homologue of the Mannich reaction, the so-called the homo-Mannich reaction, which generates the homologated γ-amino-carbonyl products, remains largely underexplored despite its potential for diverse applications. We show here a copper-catalysed homo-Mannich reaction of cyclopropanols with in situ-formed imines, furnishing a variety of chiral 2,6-disubstituted piperidines in good yields with high diastereoselectivities. Critical is the use of a diketiminate-complexed copper as the catalyst, which allows this reaction to proceed efficiently under mild conditions in an air atmosphere. Using this method as the key reaction, we achieved total synthesis of four alkaloids. This study not only expands the application range of cyclopropanol as a homoenolate equivalent for the Mannich reaction, but also inspires utilization of diketiminate ligands in metal catalysis.