文献类型：期刊文献

英文题名：Iridium-Catalyzed Diastereo- and Enantioselective [4+3] Cycloaddition of 4-Indolyl Allylic Alcohols with Azomethine Ylides

作者：Yang, Wu-Lin[1,2];Ni, Tao[1,2];Deng, Wei-Ping[1,2]

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

年份：2021

卷号：23

期号：2

起止页码：588

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000643163800061)，CCR-EXPANDED(收录号:WOS:000643163800061)】；

基金：This work is supported by the National Natural Science Foundation of China (Nos. 21772038 and 21901072) and Shanghai Sailing Program (No. 18YF140560). The authors thank the Research Center of Analysis and Test of East China University of Science and Technology for the assistance with the HRMS and NMR analyses.

语种：英文

摘要：An unprecedented iridium-catalyzed asymmetric [4 + 3] cycloaddition of racemic 4-indolyl allylic alcohols with azomethine ylides is reported. The ability of acid promoter zinc triflate to perform multiple roles is the key factor for the success of this strategy. This method provides scalable and efficient access to biologically important azepino[3,4,5-cd] indoles in good yields with generally excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). Mild reaction conditions, easily accessible substrates and chiral catalyst, and broad substrate scope highlight the practicality of this methodology.