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Issue 39, 2018
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Atom-economic synthesis of cyclobuta[a]naphthalen-4-ols via a base-promoted [2 + 2] cycloaddition/1,6-nucleophilic addition cascade

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Abstract

A first atom-economic [2 + 2] cycloaddition/1,6-conjugate addition cascade of yne-allenones with C-nucleophiles including 1,3-dicarbonyls and α,α-dicyanoolefins under base-promoted conditions has been established, enabling the direct construction of C(sp3)–C(sp3) bonds to generate cyclobuta[a]naphthalen-1-ols with generally good yields. These resulting products have a cyclobutene unit that contains both an aryl and alkyl group.

Graphical abstract: Atom-economic synthesis of cyclobuta[a]naphthalen-4-ols via a base-promoted [2 + 2] cycloaddition/1,6-nucleophilic addition cascade

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Publication details

The article was received on 20 Aug 2018, accepted on 14 Sep 2018 and first published on 19 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB02042F
Citation: Org. Biomol. Chem., 2018,16, 7104-7108
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    Atom-economic synthesis of cyclobuta[a]naphthalen-4-ols via a base-promoted [2 + 2] cycloaddition/1,6-nucleophilic addition cascade

    J. Wang, F. Xie, J. Hu, S. Yang, Y. Wang, W. Hao, S. Tu and B. Jiang, Org. Biomol. Chem., 2018, 16, 7104
    DOI: 10.1039/C8OB02042F

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