Direct Intermolecular C-H Functionalization Triggered by 1,5-Hydride Shift: Access to N-Arylprolinamides via Ugi-Type Reaction

作者：Zhen, Le; Wang, Jiankun; Xu, Qing-Long; Sun, Hongbin; Wen, Xiaoan^*; Wang, Guangji^*

来源：Organic Letters, 2017, 19(7): 1566-1569.

DOI：10.1021/acs.orglett.7b00378

• MULTICOMPONENT REACTIONS
• ARYL PYRROLES
• SHIFT/ISOMERIZATION REACTION
• BOND FUNCTIONALIZATION
• CONSTRUCTION
• CHEMISTRY
• ACIDS

A novel Ugi-type reaction triggered by 1,5-hydride shift has been established, giving access to N-atylprolinamides 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 Bronsted 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.

• 出版日期2017-4-7
• 单位中国药科大学