文献类型：期刊文献

英文题名：Aldehydes Switch Regioselectivity: a Prins Cyclization Strategy for the Synthesis of Indoline-fused THFs and Indole-fused Oxepanes

作者：Chen Xiaobei[1,2];Jiang Yuanrui[3,4];Geng Huihui[1,2];Liu Xingyu[1,2];Huang Yizhuo[1,2];Lu Jingwei[1,2];Gao Chenjing[1,2];Zhang Shilei[3,4];Zhang Jian[5];Wang Wei[1,2,6,7]

机构：[1]East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Sch Pharm, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China;[3]Soochow Univ, Jiangsu Key Lab Neuropsychiat Dis, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[4]Soochow Univ, Coll Pharmaceut Sci, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[5]Shanghai Jiao Tong Univ, Key Lab Cell Differentiat & Apoptosis, Chinese Minist Educ, Clin & Fundamental Res Ctr,Renji Hosp,Sch Med, Shanghai 200025, Peoples R China;[6]Univ Arizona, Dept Pharmacol & Toxicol, 1703 E Mabel St,POB 210207, Tucson, AZ 85721 USA;[7]Univ Arizona, BIO5 Inst, 1703 E Mabel St,POB 210207, Tucson, AZ 85721 USA

年份：2020

卷号：362

期号：13

起止页码：2620

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000532535300001)，CCR-EXPANDED(收录号:WOS:000532535300001)】；

基金：Financial support was provided by the National Natural Science Foundation of China (21572055, 21738002, 21702058, 81925034, 91753117, 81721004 and 21202112), East China University of Science and Technology, the '111' Project, Innovation Program of Shanghai Municipal Education Commission (2019-01-07-00-01-E00036), Shanghai Science and Technology Innovation (19431901600), and the Priority Academic Program Development of the Jiangsu Higher Education Institutes (PAPD).

语种：英文

外文关键词：Prins cyclization; tetrahydrofuran; oxepane; aldehyde; rearrangement

摘要：We have identified a switchable Prins cyclization process to form indoline-fused tetrahydrofurans and indole-fused oxepanes by applying different types of aldehydes under two sets of optimized conditions. Significantly, a novel Prins reaction mechanism involving an oxonium-mediated rearrangement in the formation of five-membered cyclic ethers is realized for the first time.