title: Direct Intermolecular C-H Functionalization Triggered by 1,5-Hydride Shift: Access to N-Arylprolinamides via Ugi-Type Reaction.
abstract: 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.
authors.affiliation: 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.
authors.forename: Le
authors.initials: L
authors.lastname: Zhen
authors.affiliation: 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.
authors.forename: Jiankun
authors.initials: J
authors.lastname: Wang
authors.affiliation: 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.
authors.forename: Qing-Long
authors.identifier: 0000-0003-4450-6866
authors.initials: QL
authors.lastname: Xu
authors.affiliation: 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.
authors.forename: Hongbin
authors.initials: H
authors.lastname: Sun
authors.affiliation: 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.
authors.forename: Xiaoan
authors.identifier: 0000-0001-7852-1154
authors.initials: X
authors.lastname: Wen
authors.affiliation: 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.
authors.forename: Guangji
authors.initials: G
authors.lastname: Wang