Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking.

Selective long-distance isomerization of terminal alkenes to silyl enol ethers proceeded via nondissociative chain walking using phenanthroline palladium catalysts. Notable features achieved taking advantage of the nondissociative chain walking mechanism include high efficiency obtained regardless of the chain length, high chemoselectivity toward terminal alkenes over internal ones, and retention of the stereoconfiguration of the stereocenter on the alkyl chain.