Functionalization of Alkenes with Difluoromethyl Nitrile Oxide to Access the Difluoromethylated Derivatives,Organic Letters

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Functionalization of Alkenes with Difluoromethyl Nitrile Oxide to Access the Difluoromethylated Derivatives
Organic Letters ( IF 4.9 ) Pub Date : 2024-03-18 , DOI: 10.1021/acs.orglett.4c00431
Bohdan A Chalyk _{1,

2,

3} , Oleksandr Zginnyk ₁ , Andrii V Khutorianskyi ₁ , Pavel K Mykhailiuk ₁

Affiliation

Electron-rich, electron-deficient, and non-activated alkenes can be rapidly functionalized by in situ-generated difluoromethyl nitrile oxide. The (3+2) cycloaddition proceeds at room temperature, has broad functional group tolerance, and can be used for the late-stage modification of bioactive molecules (finasteride and carbamazepine). The obtained CF₂H-isoxazolines can be easily transformed into CF₂H-containing building blocks for medicinal chemistry: amines, amino acids, amino alcohols, and spirocyclic scaffolds.

中文翻译：

用二氟甲基氧化腈对烯烃进行官能化以获得二氟甲基化衍生物

富电子、缺电子和未活化的烯烃可以通过原位生成的二氟甲基氧化腈快速官能化。 (3+2)环加成反应在室温下进行，具有广泛的官能团耐受性，可用于生物活性分子（非那雄胺和卡马西平）的后期修饰。所获得的CF ₂ H-异恶唑啉可以很容易地转化为用于药物化学的含CF ₂ H结构单元：胺、氨基酸、氨基醇和螺环支架。

更新日期：2024-03-18

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