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

Literature Information

Publication Date 2018-09-19
DOI 10.1039/C8OB02042F
Impact Factor 3.876
Authors

Jia-Yin Wang, Feng-Lie Xie, Jian-Qiang Hu, Shi-Zhao Yang, You-Jian Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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