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<p>We report the highly enantioselective nucleophilic addition reaction of simple ketone-derived hydrazones. Accordingly, a ErCl₃-catalyzed cyanation of both aliphatic and aryl ketone hydrazones is achieved for the facile access of C<sup>α</sup>-tetrasubstituted α-hydrazino nitriles in up to 96% ee, by using the sterically confined pyridinebisoxazoline (PYBOX) ligand featuring a sulfonyl group at the pyridine C4 position. This method enables the shortest catalytic enantioselective total synthesis of <i>L-carbidopa</i>, a drug that could treat the symptoms of Parkinson’s disease, with 82% overall yield in four steps. These adducts are valuable synthons to various α-tertiary hydrazines and related azacycles that are interesting targets for medicinal studies and pesticide research. From our biological analysis, a chiral α-hydrazino nitrile with good insecticidal activity against <i>Aphis gossypii</i> (LC<sub>50</sub> = 15.11 mg∙L<sup>–1</sup>) was identified, rivaling commercial insecticides.</p>

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Sulfonyl-PYBOX/ErCl3 complex enable highly enantioselective synthesis of α,α-dialkyl and α-alkyl-α-aryl hydrazinonitriles

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年6月18日

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  • Yi Gong,
  • Zheng Zhang,
  • Qiang Cao,
  • Cai Wang,
  • Min-Chuan Jiang,
  • Zhi-Heng Qiu,
  • Xiao-Jing Le,
  • Yu-Jie Ye,
  • Tao Wang,
  • Yun-Hao Tang,
  • Ying Zhang,
  • Haoran Zhao,
  • Li Cui,
  • Feng Zhou,
  • Bo-Shuai Mu,
  • Xin Wang,
  • Jian Zhou

摘要

We report the highly enantioselective nucleophilic addition reaction of simple ketone-derived hydrazones. Accordingly, a ErCl₃-catalyzed cyanation of both aliphatic and aryl ketone hydrazones is achieved for the facile access of Cα-tetrasubstituted α-hydrazino nitriles in up to 96% ee, by using the sterically confined pyridinebisoxazoline (PYBOX) ligand featuring a sulfonyl group at the pyridine C4 position. This method enables the shortest catalytic enantioselective total synthesis of L-carbidopa, a drug that could treat the symptoms of Parkinson’s disease, with 82% overall yield in four steps. These adducts are valuable synthons to various α-tertiary hydrazines and related azacycles that are interesting targets for medicinal studies and pesticide research. From our biological analysis, a chiral α-hydrazino nitrile with good insecticidal activity against Aphis gossypii (LC50 = 15.11 mg∙L–1) was identified, rivaling commercial insecticides.