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Gold(I) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)

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Abstract

A gold-catalyzed cascade cyclization of vinylidenecyclopropanes (VDCPs) bearing a naphthyl moiety and an ortho-alkoxylmethyl group has been reported in this paper, affording spiro[cyclopenta[a]naphthalene-1,1′-cyclopropanes] in moderate to good yields. The reaction proceeded through a two-fold intramolecular nucleophilic addition (O-nucleophilic addition and then Caryl-nucleophilic addition) to a vinylidenecyclopropane moiety to give a highly strained intermediate and subsequent retro-Diels–Alder addition. The reaction mechanism has been investigated on the basis of a deuterium labeling experiment, mass spectrometric investigation and DFT calculation.

Graphical abstract: Gold(i) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)

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Publication details

The article was received on 15 Aug 2017, accepted on 27 Sep 2017 and first published on 28 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00722A
Citation: Org. Chem. Front., 2018, Advance Article
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    Gold(I) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)

    W. Zang, Y. Wei and M. Shi, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00722A

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