He Ciwang, Cai Ju, Zheng Yang, Pei Chao, Qiu Lihua, Xu Xinfang
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
ACS Omega. 2019 Sep 9;4(13):15754-15763. doi: 10.1021/acsomega.9b02693. eCollection 2019 Sep 24.
A one-pot gold-catalyzed hydroalkoxylation/Povarov reaction cascade of alkynols with -aryl imines or in situ generated iminium has been developed. The protocol provides a facile access to a series of fused tricyclic tetrahydroquinolines with a broad substrate scope using readily available materials under mild conditions. The unique mechanistic feature is the dual function of the gold catalyst, which first catalyzed the intramolecular hydroalkoxylation of alkynols, and upon the formation of dihydrofuran species, promoted the following Povarov reaction with high stereoselectivity.
已开发出一种一锅法金催化的炔醇与芳基亚胺或原位生成的亚胺离子的氢烷氧基化/波瓦罗夫反应串联反应。该方法使用易得的原料在温和条件下为一系列具有广泛底物范围的稠合三环四氢喹啉提供了一种简便的合成途径。独特的机理特征是金催化剂的双重功能，它首先催化炔醇的分子内氢烷氧基化反应，在二氢呋喃物种形成后，以高立体选择性促进随后的波瓦罗夫反应。
