文献类型：期刊文献

英文题名：Enantioselective construction of tricyclic pyrrolidine-fused benzo[b] thiophene 1,1-dioxide derivatives via copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition

作者：Deng, Hua;He, Fu-Sheng;Li, Cong-Shan;Yang, Wu-Lin;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：2017

卷号：4

期号：12

起止页码：2343

外文期刊名：ORGANIC CHEMISTRY FRONTIERS

收录：;EI(收录号：20184806137352);WOS:【SCI-EXPANDED(收录号:WOS:000416065700009)，CCR-EXPANDED(收录号:WOS:000416065700009)】；

基金：This work is supported by the National Natural Science Foundation of China (no. 21372074 and 21572053).

语种：英文

外文关键词：Catalysis - Copper compounds - Enantioselectivity

摘要：A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with benzo[b] thiophene 1,1-dioxides as the dipolarophiles was developed, providing elegant access to novel chiral tricyclic pyrrolidine-fused benzo[b] thiophene 1,1-dioxide derivatives in good to excellent yields (up to 99%) with excellent diastereo- and enantioselectivities (up to > 25 : 1 dr, up to 99% ee). Furthermore, the cycloadducts could be conveniently converted to synthetically important tricyclic pyrrolidine-fused benzo[b] thiophene and tetracyclic oxazolidin-2-one derivatives via simple transformations.