文献类型：期刊文献

英文题名：Cu(I)-Catalyzed Chemoselective and Stereoselective [3+3] Cycloaddition of Azomethine Ylides with 2-Indolylnitroethylenes: Facile Access to Highly Substituted Tetrahydro-γ-Carbolines

作者：Yang, Wu-Lin;Li, Chun-Yan;Qin, Wen-Jing;Tang, Fei-Fei;Yu, Xingxin;Deng, Wei-Ping[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2016

卷号：6

期号：9

起止页码：5685

外文期刊名：ACS CATALYSIS

收录：;EI(收录号：20163602781736);WOS:【SCI-EXPANDED(收录号:WOS:000382714000007)】；

基金：This work is supported by the National Natural Science Foundation of China (No. 21372074), the Shanghai Committee of Science and Technology (Nos. 14431902500, 14PJD013), and Shanghai Yangfan Program (No. 14YF1404600).

语种：英文

外文关键词：asymmetric catalysis; chemoselectivity; cycloaddition; azomethine ylide; tetrahydro-gamma-carboline

摘要：A Cu(I)-catalyzed asymmetric [3 + 3] cycloaddition of azomethine ylides with 2-indolylnitroethylenes is described. Challenges confronted in this reaction include chemoselectivity between [3 + 2] cycloaddition and [3 + 3] cycloaddition, reactivity and stereoselectivity of intramolecular Friedel Crafts reaction, and enantioselective control for constructing tetrahydro-gamma-carbolines bearing multiple stereocenters. In the presence of copper(I)/Ph-Phosferrox complex, an array of chiral tetrahydro-gamma-carboline compounds was generally obtained in moderate to high yields (up to 92%) with moderate to high chemoselectivities (up to 94:6 cr) and a high level of stereoselectivity (up to >98:2 dr, >99% ee in most cases). [Here, cr is the chemoselectivity ratio, dr is the diastereoisomeric ratio, and ee is enantiomeric excess.]