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Issue 19, 2014
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Cooperative N-heterocyclic carbene (NHC)–Lewis acid-mediated regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes with isatins

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Abstract

A novel and regioselective umpolung synthesis of spirooxindoles has been developed by cooperative NHC–Lewis acid-mediated formal [3 + 2] annulations of alkynyl aldehydes with isatins. In most cases, the reactions proceeded via a3–d3 umpolung of alkynyl aldehydes resulting in spirooxindole butenolides. In a few cases, spirooxindole furan-3(2H)-ones were formed as the major products via an a1–d1 umpolung process by controlling the reaction temperature. These newly formed spirooxindoles could provide promising candidates for chemical biology and drug lead discovery.

Graphical abstract: Cooperative N-heterocyclic carbene (NHC)–Lewis acid-mediated regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes with isatins

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Publication details

The article was received on 20 Jan 2014, accepted on 13 Mar 2014 and first published on 14 Mar 2014


Article type: Communication
DOI: 10.1039/C4OB00145A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 3009-3015
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    Cooperative N-heterocyclic carbene (NHC)–Lewis acid-mediated regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes with isatins

    Y. Zhang, Y. Lu, W. Tang, T. Lu and D. Du, Org. Biomol. Chem., 2014, 12, 3009
    DOI: 10.1039/C4OB00145A

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