Cycloisomerization of dienes with carbophilic lewis acids: mimicking terpene biosynthesis with Pt(II) catalysts.
[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.
Kerber
William D
WD
Department of Chemistry, University of North Carolina at Chapel Hill, 27599-3290, USA.
Gagné
Michel R
MR
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D010984:Platinum / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D039821:Monoterpenes; C035126:thujane; D010984:Platinum