Use of β-Amido Allylboronate as a Nucleophilic Reagent in Catalytic Amide Allylation of N-Carbonyl Imides
Use of β-Amido Allylboronate as a Nucleophilic Reagent in Catalytic Amide Allylation of N-Carbonyl Imides
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DOI：
10.1002/ejoc.201701112
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发表时间：
2017-11-02
影响因子：
2.8
通讯作者：
Yoda, Hidemi
中科院分区：
文献类型：
--
作者：
Sengoku, Tetsuya;Kamiya, Yuta;Yoda, Hidemi
该通讯描述了 β-酰胺基烯丙基硼酸酯作为亲核试剂在 N-羰基酰亚胺的催化酰胺烯丙基化中的用途。酰亚胺底物与硼酸酯的反应是通过使用催化溴化锌和碱性添加剂（乙醇、碳酸钾和18冠6-醚）完成的，通过开环-重合过程得到氮杂螺-γ-内酯，收率高达100%。这里建立的具有成本效益且易于操作的方法可以耐受克级合成，而不会显着损失反应效率。
This communication describes the utility of beta-amido allylboronate as a nucleophile in the catalytic amide allylation of N-carbonyl imides. The reaction of the imide substrates with the boronates has been accomplished by using catalytic zinc bromide and basic additives (ethanol, potassium carbonate and 18-crown 6-ether), affording azaspiro-gamma-lactones through a ring opening-reclosure process with yields up to 100%. The cost-effective and easy-to-handle method established here tolerated for gram-scale synthesis without significant loss of reaction efficiency.