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Issue 6, 2017
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Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives

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Abstract

A phosphine-mediated domino reaction between phthalimidomalonates and allenoates furnishes highly functionalized pyrroloisoindolinone derivatives in synthetically useful yields. When ethyl but-2-ynoate was reacted with phthalimidomalonates under the same conditions, pyrroloisoindolinone derivatives were also obtained in good to excellent yields. The mechanism for the transformation is a tandem γ-umpolung/Wittig/γ-umpolung process. The present domino reaction not only exploits the potential of allenoates, but also extends the existing phosphine-mediated cyclization scope.

Graphical abstract: Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives

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Publication details

The article was received on 02 Dec 2016, accepted on 02 Jan 2017 and first published on 04 Jan 2017


Article type: Research Article
DOI: 10.1039/C6QO00775A
Citation: Org. Chem. Front., 2017,4, 967-971
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    Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives

    Z. Huang, Q. Chen, X. Yang, Y. Liu, L. Zhang, T. Lu and Q. Zhou, Org. Chem. Front., 2017, 4, 967
    DOI: 10.1039/C6QO00775A

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