Key Laboratory of Drug Metabolism and Pharmacokinetics and ‡Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, China Pharmaceutical University , 24 Tongjia Xiang, Nanjing 210009, Jiangsu, China.
Org Lett. 2017 Apr 7;19(7):1566-1569. doi: 10.1021/acs.orglett.7b00378. Epub 2017 Mar 14.
A novel Ugi-type reaction triggered by 1,5-hydride shift has been established, giving access to N-arylprolinamides and related compounds in high atom economy and good yields. This is an example of a two starting material-three component reaction. The benzyl alcohol substrate 1 acts as a dual synthon, which upon treatment with a Brønsted acid affords iminium ion and water. Nucleophilic attack at the iminium ion by the third component isocyanide, followed by hydrolysis with the endogenic water, gives the Ugi-type reaction products. The reaction proceeds under mild conditions and is tolerable to a broad scope of substrates.
建立了一种新型的由 1,5-氢迁移引发的 Ugi 型反应，以高原子经济性和良好的收率得到 N-芳基脯氨酰胺和相关化合物。这是一个两个起始原料-三个组分反应的例子。苄醇底物 1 作为双合成子，用布朗斯特酸处理后得到亚胺离子和水。亲核试剂进攻亚胺离子，然后与内源性水发生水解反应，得到 Ugi 型反应产物。该反应在温和条件下进行，对广泛的底物具有耐受性。
