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Issue 22, 2017
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Construction of polycyclic frameworks via a DMAP-catalysed tandem addition–(4 + 2) annulation sequence of δ-acetoxy allenoate

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Abstract

Here is reported the DMAP-catalyzed addition/(4 + 2) annulation domino reaction of δ-acetoxy allenoate with either salicylaldehyde-derived oxadiene or pyrrolealdehyde-derived oxadiene, which provides a facile method toward polycyclic frameworks. A cationic intermediate, 3-ammonium-2,4-dienoate, is proposed to be involved via an addition–elimination process between an allenoate and a catalyst, which is capable of undergoing addition with either O- or N-nucleophile and subsequent (4 + 2) annulation with oxadiene.

Graphical abstract: Construction of polycyclic frameworks via a DMAP-catalysed tandem addition–(4 + 2) annulation sequence of δ-acetoxy allenoate

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Publication details

The article was received on 21 Mar 2017, accepted on 10 Apr 2017 and first published on 10 Apr 2017


Article type: Communication
DOI: 10.1039/C7OB00688H
Citation: Org. Biomol. Chem., 2017,15, 4807-4810
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    Construction of polycyclic frameworks via a DMAP-catalysed tandem addition–(4 + 2) annulation sequence of δ-acetoxy allenoate

    C. Ni, Y. Yuan, Y. Zhang, J. Chen, D. Wang and X. Tong, Org. Biomol. Chem., 2017, 15, 4807
    DOI: 10.1039/C7OB00688H

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