Abstract
A ruthenium-catalyzed hydrative cyclization of enynes has been developed. The reaction converts a range of 1,5-enynes bearing terminal alkyne and Michael acceptor moieties into cyclopentanone derivatives. From extensive catalyst screening experiments, a trinuclear ruthenium complex, [Ru3(dppm)3Cl5]PF6, has been identified to be an effective catalyst in mediating the 1,1-difunctionalization of alkynes. It is proposed that this novel umpolung reaction proceeds through the formation of a ruthenium vinylidene, anti-Markovnikov hydration, and intramolecular Michael addition of an acyl ruthenium to the alkene.
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