文献类型：期刊文献

英文题名：Regioselective and Stereoselective [3+3] Annulation of Ketones Derived Azomethine Ylides with 2-Indolylethylenes: Direct Access to Highly Substituted Tetrahydro--Carbolines

作者：Liu, Yang-Zi[1,2];Shang, Shao-Jing[1,2];Zhu, Jing-Yan[1,2];Yang, Wu-Lin[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：11

起止页码：2191

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000434349400019)，CCR-EXPANDED(收录号:WOS:000434349400019)】；

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

语种：英文

外文关键词：asymmetric catalysis; regioselectivity; [3+3] annulation; azomethine ylide; tetrahydro--carboline

摘要：A highly efficient asymmetric [3+3] annulation of ketones derived azomethine ylides with 2-indolylethylenes is reported, which is achieved by catalytic Michael addition in the presence of Ag(I)/Ph-Phosferrox complex and subsequent BF3Et2O promoted Friedel-Crafts tandem reaction in a one-pot process. This strategy addresses the challenge of selectivity between [3+2] cycloaddition and [3+3] annulation and exclusively affords a series of [3+3] cycloadducts, highly substituted tetrahydro--carbolines in excellent yields (up to 99%), with excellent levels of regioselectivities and stereoselectivities (>20:1 rr, up to >20:1 dr; up to 99%ee).