通过氧化C-H环化和串联[4 + 2]环加成反应直接构建桥连多环骨架
Direct Access to Bridged Polycyclic Skeletons by Merging Oxidative C-H Annulation and Cascade [4 + 2] Cycloaddition.
作者信息
He Yan, Wang Heng, Xu Li, Li Deng-Yuan, Ge Ji-Hong, Feng Da-Fu, Feng Wei, Zou Gang, Liu Pei-Nian
机构信息
Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, China.
School of Materials and Chemical Engineering, Xuzhou University of Technology, Xuzhou 221018, China.
出版信息
Org Lett. 2022 Jan 14;24(1):121-126. doi: 10.1021/acs.orglett.1c03652. Epub 2021 Dec 21.
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(1)-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.
我们报道了一种通过将氧化C-H环化和串联环加成相结合来直接合成桥连多环骨架的逐步经济策略。在该方案中，首先通过亚乙基氧化吲哚与炔烃的氧化C-H环化反应合成了螺[环戊烷-1,3'-吲哚啉]-2,4-二烯-2'-酮。随后与亲双烯体进行串联[4 + 2]环加成反应，得到桥连双环[2.2.1]喹啉-2(1)-酮，并实现了两个季碳中心和三个C-C键的一锅构建。对后者的机理研究表明，这是一个串联开环、1,5-西格玛重排和[4 + 2]环加成过程。
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