Lewis Acid Catalyzed Tandem 1,4-Conjugate Addition/Cyclization of in Situ Generated Alkynyl o‑Quinone Methides and Electron-Rich Phenols: Synthesis of Dioxabicyclo[3.3.1]nonane Skeletons

A versatile Lewis acid catalyzed tandem cyclization of in situ generated alkynyl o-quinone methides (o-AQMs) with electron-rich phenols has been developed on the basis of the mode involving an intermolecular 1,4-conjugate addition/6-endo cyclization/1,3-aryl shift/intramolecular 1,4-conjugate additi...

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Bibliographic Details
Published in:Organic letters 2018-07, Vol.20 (14), p.4371-4374
Main Authors: Du, Ji-Yuan, Ma, Yan-Hua, Meng, Fan-Xiao, Chen, Bao-Li, Zhang, Shao-Liang, Li, Qian-Li, Gong, Shu-Wen, Wang, Da-Qi, Ma, Chun-Lin
Format: Article
Language:English
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Summary:A versatile Lewis acid catalyzed tandem cyclization of in situ generated alkynyl o-quinone methides (o-AQMs) with electron-rich phenols has been developed on the basis of the mode involving an intermolecular 1,4-conjugate addition/6-endo cyclization/1,3-aryl shift/intramolecular 1,4-conjugate addition cascade. This reaction provides a new method for expeditious assembly of synthetically and biologically interesting tetracyclic bridged dioxabicyclo[3.3.1]­nonane skeletons featuring a congested bridgehead oxa-quaternary stereocenter.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01862