文献类型：期刊文献

英文题名：Direct Access of the Chiral Quinolinyl Core of Cinchona Alkaloids via a Bronsted Acid and Chiral Amine Co-catalyzed Chemo- and Enantioselective α-Alkylation of Quinolinylmethanols with Enals

作者：Tong, Mengchao[1,2];Wang, Sinan[1,2];Zhuang, Jinchen[1,2];Qin, Cong[1,2];Li, Hao[1,2];Wang, Wei[1,2,3]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, State Key Lab Bioengn Reactor, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[3]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2018

卷号：20

期号：4

起止页码：1195

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000426013600075)，CCR-EXPANDED(收录号:WOS:000426013600075)】；

基金：This work was supported by the National Natural Science Foundation of China (21738002, 21572054, and 21572055), the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the Fundamental Research Funds for the Central Universities, and the China 111 Project (Grant B07023).

语种：英文

摘要：A strategy for the facile construction of the chiral quinolinylmethanolic structure, a core featured in cinchona alkaloids, is reported. A new reactivity is harnessed by TfOH-promoted chemoselective activation of alpha-C-H over O-H bond in quinolinylmethanols. The new reactivity is successfully engineered with an iminium catalysis in a synergistic manner to create a powerful conjugate addition-cyclization cascade process for synthesis of chiral quinoline derived gamma-butyrolactones in good yields and with good to excellent enantioselectivities. The method enables the first total synthesis of natural product broussonetine in three steps.