文献类型：期刊文献

英文题名：Direct Access to Bridged Polycyclic Skeletons by Merging Oxidative C-H Annulation and Cascade [4+2] Cycloaddition

作者：He, Yan[1,2];Wang, Heng[1];Xu, Li[1];Li, Deng-Yuan[1];Ge, Ji-Hong[1];Feng, Da-Fu[1];Feng, Wei[1];Zou, Gang[1];Liu, Pei-Nian[1]

机构：[1]East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Key Lab Adv Mat, Sch Chem & Mol Engn,Shanghai Key Lab Funct Mat Ch, Shanghai 200237, Peoples R China;[2]Xuzhou Univ Technol, Sch Mat & Chem Engn, Xuzhou 221018, Jiangsu, Peoples R China

年份：2022

卷号：24

期号：1

起止页码：121

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000736002800001)】；

基金：This work was supported by the National Natural Science Foundation of China (Nos. 21925201, 91845110 and 21978049), Natural Science Foundation of Shanghai (20ZR1414200), the Program for Eastern Scholar Distinguished Professor and the Fundamental Research Funds for the Central Universities. We thank the Research Center of Analysis and Test of East China University of Science and Technology for help in the characterization.

语种：英文

摘要：We report a step-economic strategy for the direct synthesis of bridged polycyclic skeletons by merging oxidative C-H annulation and cascade cycloaddition. In the protocol, spiro[cyclopentane-1,3'-indoline]-2,4-dien-2'-ones were first synthesized by oxidative C-H annulation of ethylideneoxindoles with alkynes. Subsequent cascade [4 + 2] cycloaddition with dienophiles gave the bridged bicyclo[2.2.1]quinolin-2(1H)-ones and enabled the one-pot construction of two quaternary carbon centers and three C-C bonds. Mechanistic investigations of the latter suggest a cascade ring-opening, 1,5-sigmatropic rearrangement, and [4 + 2] cycloaddition process.