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Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction

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Abstract

An unprecedented strategy of a rhodium-catalysed redox-neutral cascade reaction starting from benzamides and cyclopropenones via addition of a C–H bond into a polar carbonyl group for the rapid assembly of cyclopentene spiroisoindolinones has been developed. Water was produced as the sole by-product. Metal migration and abstraction of a H-atom from the arylcyclopropenone's aromatic ring are the key steps in building the spirocycle. Two C–C bonds, one C–N bond and an N-substituted quaternary carbon center were formed sequentially in a one pot manner.

Graphical abstract: Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction

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Publication details

The article was received on 09 Oct 2018, accepted on 26 Oct 2018 and first published on 30 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC08081J
Citation: Chem. Commun., 2019, Advance Article
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    Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction

    T. Yuan, C. Pi, C. You, X. Cui, S. Du, T. Wan and Y. Wu, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC08081J

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