Ruthenium-Catalyzed Hydrative Cyclization of 1,5-Enynes

Yiyun Chen, Douglas M. Ho, and Chulbom Lee*
Department of Chemistry, Princeton University, Princeton, New Jersey, 08544-1009
J. Am. Chem. Soc., 2005, 127 (35), pp 12184–12185
DOI: 10.1021/ja053462r
Publication Date (Web): August 12, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, cblee@princeton.edu

Abstract

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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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History

  • Published In Issue September 07, 2005
  • Received May 27, 2005

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