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Issue 10, 2015
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Gold(I)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes

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Abstract

Gold catalyzed cycloisomerization of aromatic ring tethered vinylidenecyclopropane-enes provides a divergent synthetic protocol for the construction of O-containing fused heterocycles through controllable carbene or non-carbene related processes. The carbene induced process features a new amphiphilic strategy to generate a gold carbene via a rearrangement of vinylidenecyclopropane. Whereas, the electronic effect of the ortho-substituents switches the reaction mode onto the non-carbene related process, from which five- or six-membered rings are selectively produced through allyl-migration.

Graphical abstract: Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes

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Publication details

The article was received on 19 May 2015, accepted on 23 Jun 2015 and first published on 24 Jun 2015


Article type: Edge Article
DOI: 10.1039/C5SC01806D
Citation: Chem. Sci., 2015,6, 5519-5525
  • Open access: Creative Commons BY license
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    Gold(I)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes

    D. Li, Y. Wei, I. Marek, X. Tang and M. Shi, Chem. Sci., 2015, 6, 5519
    DOI: 10.1039/C5SC01806D

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