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Synlett 2023; 34(20): 2417-2422
DOI: 10.1055/a-2123-7565
DOI: 10.1055/a-2123-7565
cluster
Special Issue Dedicated to Prof. Hisashi Yamamoto
Acid-Catalyzed [4+1]-Dearomatization Spiroannulation of Hydroquinones and Naphthols
Financial support for this work was generously provided by ShanghaiTech University.
Dedicated to the 80th birthday of Professor Hisashi Yamamoto.
Abstract
Acid-catalyzed [4+1]-dearomatization spiroannulation reactions of electron-rich hydroquinone and naphthol derivatives were demonstrated as convenient methods to access spirocyclic cyclohexadienone derivatives. The Lewis acid Bi(OTf)3 exhibited the best catalytic performance when a 1,2-dialkynylbenzene was used as the electrophile for the spiroannulation, whereas the Brønsted acid benzene-1,2-disulfonic acid was the best catalyst when 2-ethynylbenzylic esters were used as electrophiles. Most of the reaction conditions are mild, efficient, and simple to operate.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2123-7565.
- Supporting Information
Publikationsverlauf
Eingereicht: 30. April 2023
Angenommen nach Revision: 05. Juli 2023
Accepted Manuscript online:
05. Juli 2023
Artikel online veröffentlicht:
29. August 2023
© 2023. Thieme. All rights reserved
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References and Notes
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3′-Hydroxy-1,3-bis(methylene)-1,3-dihydro-2′H-spiro[indene-2,1′-naphthalen]-2′-one (3af): Typical Procedure
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