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<p>Chiral aliphatic amines bearing vicinal stereocenters are prevalent motifs in pharmaceuticals and bioactive molecules, yet efficient and stereodivergent access to these structures remains a longstanding challenge. Herein, we report a nickel-catalyzed enantioselective hydroamination of acyclic trisubstituted alkenes that provides a unified platform for the stereodivergent construction of chiral amines bearing β,γ-stereocenters. The reaction exhibits broad substrate scope, accommodating diverse amine electrophiles and tri-substituted alkenes, including those derived from complex bioactive molecules, with high levels of regio-, diastereo-, and enantioselectivity. By modulating the alkene geometry and the configuration of a chiral biimidazoline ligand, all four stereoisomers can be accessed in a predictable manner. The protocol proceeds under mild conditions, tolerates various functional groups, and enables late-stage derivatization, demonstrating its utility for constructing densely functionalized, three-dimensional amine scaffolds. This work provides a valuable platform for asymmetric synthesis and holds strong potential for drug discovery and molecular design.</p>

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Stereodivergent synthesis of chiral amines bearing vicinal stereocenters via hydroamination of trisubstituted alkenes

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年3月4日

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  • Haohao Bai,
  • Mingchao Li,
  • Xiuping Wang,
  • Tao Jiang,
  • Lintao Zeng,
  • Lanlan Zhang,
  • Chao Wang

摘要

Chiral aliphatic amines bearing vicinal stereocenters are prevalent motifs in pharmaceuticals and bioactive molecules, yet efficient and stereodivergent access to these structures remains a longstanding challenge. Herein, we report a nickel-catalyzed enantioselective hydroamination of acyclic trisubstituted alkenes that provides a unified platform for the stereodivergent construction of chiral amines bearing β,γ-stereocenters. The reaction exhibits broad substrate scope, accommodating diverse amine electrophiles and tri-substituted alkenes, including those derived from complex bioactive molecules, with high levels of regio-, diastereo-, and enantioselectivity. By modulating the alkene geometry and the configuration of a chiral biimidazoline ligand, all four stereoisomers can be accessed in a predictable manner. The protocol proceeds under mild conditions, tolerates various functional groups, and enables late-stage derivatization, demonstrating its utility for constructing densely functionalized, three-dimensional amine scaffolds. This work provides a valuable platform for asymmetric synthesis and holds strong potential for drug discovery and molecular design.