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Issue 2, 2012
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Selective formation of angular tricyclic compounds by ruthenium-mediated ring-rearrangement metathesis

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Abstract

Unsaturated spirocyclic substrates bearing two alkenyl chains underwent ruthenium-mediated ring-rearrangement metathesis through relaying cyclohexene and cycloheptene moieties to give angularly fused tricyclics. In some instances where two products were expected, high degrees of selectivity were observed. In one instance the structural parameter leading to selectivity was very subtle; in others the transformation favoured the formation of products with a cis-fused cyclohexene moiety. An unusual transformation involving ring-opening, double-bond migration, and then ring-closing was observed.

Graphical abstract: Selective formation of angular tricyclic compounds by ruthenium-mediated ring-rearrangement metathesis

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Publication details

The article was received on 01 Sep 2011, accepted on 25 Oct 2011 and first published on 15 Nov 2011


Article type: Communication
DOI: 10.1039/C1CC15452D
Chem. Commun., 2012,48, 233-235

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    Selective formation of angular tricyclic compounds by ruthenium-mediated ring-rearrangement metathesis

    F. Gao, C. T. M. Stamp, P. D. Thornton, T. S. Cameron, L. E. Doyle, D. O. Miller and D. J. Burnell, Chem. Commun., 2012, 48, 233
    DOI: 10.1039/C1CC15452D

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