Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines
Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines
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DOI：
10.1021/jo300433a
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发表时间：
2012-04-20
影响因子：
3.6
通讯作者：
Doyle, Abigail G.
中科院分区：
文献类型：
--
作者：
Kalow, Julia A.;Schmitt, Dana E.;Doyle, Abigail G.
刘易斯碱催化促进由苯甲酰氟和非亲核醇原位生成胺-HF试剂。描述了使用这种潜在的HF源将氮丙啶氢化以提供β-氟胺。该方案显示了氮丙啶取代和N-保护基团的广泛范围。提供了区域选择性和非对映选择性开环以获得医学上相关的β-氟胺结构单元的实例。
Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide beta-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant beta-fluoroamine building blocks are presented.