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. 2005 Jul 21;7(15):3379-81.
doi: 10.1021/ol051277c.

Cycloisomerization of dienes with carbophilic lewis acids: mimicking terpene biosynthesis with Pt(II) catalysts

William D Kerber  1 , Michel R Gagné
Affiliations

Cycloisomerization of dienes with carbophilic lewis acids: mimicking terpene biosynthesis with Pt(II) catalysts

William D Kerber et al. Org Lett. .

Abstract

[reaction: see text]. Dicationic Pt(II) complexes containing triphosphine pincer ligands are excellent catalysts for the cycloisomerization of 1,6- and 1,7-dienes into bicyclopropane carbocycles. In analogy to the biosynthetic route to these monoterpene-like compounds, carbocation intermediates are proposed and supported by trapping experiments. Reactivation of the trapped intermediates indicates that cation generation by C-C bond formation is both rapid and reversible.

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Figures

Scheme 1
Scheme 1
Trapping of carbocationic intermediates
Scheme 2
Scheme 2
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