文献类型：期刊文献

英文题名：Enantioselective Synthesis of Tropanes via [3+3] Annulation of Cyclic Azomethine Ylides with Substituted 2-Vinylindoles and 2-Vinylpyrroles

作者：Zheng, Xing[1,2];Yang, Wu-Lin[1,2];Liu, Yang-Zi[1,2];Wu, Shu-Xiao[1,2];Deng, Wei-Ping[1,2]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2018

卷号：360

期号：15

起止页码：2843

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000440815900010)，CCR-EXPANDED(收录号:WOS:000440815900010)】；

基金：This work is supported by the National Natural Science Foundation of China (No. 21772038), Shanghai Sailing Program (No. 18YF140560), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：asymmetric catalysis; [3+3] annulation; azomethine ylides; 2-vinylindoles; tropanes

摘要：A novel strategy for constructing tropanes via [3+3] annulation of cyclic azomethine ylides with substituted 2-vinylindoles and 2-vinylpyrroles in the presence of in-house Cu(II)/N,O-ligand complex has been developed. The reaction was achieved via a tandem copper(II)-catalyzed Michael addition/BF3 center dot Et2O promoted intramolecular aza-Friedel-Crafts reaction of indoles or pyrroles with non-activated ketimines, providing indole or pyrrole-annulated tropanes in high yields (up to 87%) and excellent stereoselectivities (>99:1 dr in all cases, up to >99% ee).