文献类型：期刊文献

英文题名：Organocatalytic Regiodivergent Ring Expansion of Cyclobutanones for the Enantioselective Synthesis of Azepino[1,2-a]indoles and Cyclohepta[b]indoles

作者：Yang, Wu-Lin[1,2];Li, Wen[1,2];Yang, Zhong-Tao[1,2];Deng, Wei-Ping[1,2,3]

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;[3]Zhejiang Normal Univ, Dept Chem, Minist Educ Adv Catalysis Mat, Key Lab, Jinhua 321004, Zhejiang, Peoples R China

年份：2020

卷号：22

期号：10

起止页码：4026

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000535292300058)，CCR-EXPANDED(收录号:WOS:000535292300058)】；

基金：This work is supported by the National Natural Science Foundation of China (nos. 21572053 and 21772038) and the China Postdoctoral Science Foundation (nos. 2018M632037 and 2019T120310). We greatly appreciate the Research Center of Analysis and Test of East China University of Science and Technology for the assistance with the MS and NMR analysis.

语种：英文

摘要：A regiodivergent organocatalytic enantioselective Michael addition/three-atom ring expansion sequence of electron-withdrawing group activated cyclobutanones with 2-nitrovinylindoles was developed. A series of azepino[1,2-a]indoles were obtained with exclusive regioselectivities and high diastereo- and enantioselectivities (up to >20:1 dr, 96% ee) with the application of the N1 nucleophilic site of the indole nucleus. Meanwhile, various cyclohepta[b]indoles could be accessed with high enantiopurity (up to 96% ee) through the Michael addition/boron-trifluoride-etherate-promoted indole C-3-attack ring expansion process.