磺酰基PYBOX/ErCl3配合物能够高度选择性地合成α、α-二烷基和α-烷基-α-芳基肼腈
{"_":"Sulfonyl-PYBOX/ErCl complex enable highly enantioselective synthesis of α,α-dialkyl and α-alkyl-α-aryl hydrazinonitriles.","sub":["3"]}
摘要(中文译文)
我们报道了简单酮衍生腙的高对映选择性亲核加成反应。据此，利用在吡啶C4位带有磺酰基的空间受限吡啶双噁唑啉（PYBOX）配体，实现了ErCl₃催化的脂肪酮腙和芳基酮腙的氰化反应，可便捷地获得高达96% ee的C-四取代α-肼基腈。该方法实现了L-卡比多巴的最短催化对映选择性全合成，该药物可用于治疗帕金森病症状，四步反应总收率为82%。这些加合物是合成各种α-叔肼及相关氮杂环的宝贵合成子，这些化合物是药物研究和农药研究中颇具吸引力的目标。通过我们的生物学分析，鉴定出一种对棉蚜具有良好杀虫活性的手性α-肼基腈（LC = 15.11 mg∙L），其活性可与商业杀虫剂相媲美。
Abstract
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-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 (LC = 15.11 mg∙L) was identified, rivaling commercial insecticides.
如何引用
AMA
Yi Gong, Zheng Zhang, Qiang Cao, Cai Wang, Min-Chuan Jiang, Zhi-Heng Qiu, et al. {"_":"Sulfonyl-PYBOX/ErCl complex enable highly enantioselective synthesis of α,α-dialkyl and α-alkyl-α-aryl hydrazinonitriles.","sub":["3"]}. Nature communications. 2026; doi:10.1038/s41467-026-74600-0.
APA
Yi Gong, Zheng Zhang, Qiang Cao, Cai Wang, Min-Chuan Jiang, Zhi-Heng Qiu, et al (2026). {"_":"Sulfonyl-PYBOX/ErCl complex enable highly enantioselective synthesis of α,α-dialkyl and α-alkyl-α-aryl hydrazinonitriles.","sub":["3"]}. Nature communications. https://doi.org/10.1038/s41467-026-74600-0
GB/T 7714
Yi Gong, Zheng Zhang, Qiang Cao, Cai Wang, Min-Chuan Jiang, Zhi-Heng Qiu, et al. {"_":"Sulfonyl-PYBOX/ErCl complex enable highly enantioselective synthesis of α,α-dialkyl and α-alkyl-α-aryl hydrazinonitriles.","sub":["3"]}[J]. Nature communications, 2026 doi:10.1038/s41467-026-74600-0.
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