Issue 2, 2012

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

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

Supplementary files

Article information

Article type
Communication
Submitted
01 Sep 2011
Accepted
25 Oct 2011
First published
15 Nov 2011

Chem. Commun., 2012,48, 233-235

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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