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, Email: cblee
princeton.edu
Y. Chen, D. M. Ho, C. Lee, J. Am. Chem. Soc., 2005, 127, 12184-12185.
DOI: 10.1021/ja053462r (free Supporting Information)
Abstract
A ruthenium-catalyzed hydrative cyclization converts a range of 1,5-enynes bearing terminal alkyne and Michael acceptor moieties into cyclopentanone derivatives. 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.
see article for more examples
proposed mechanism
Key Words
cyclopentanones, hydration, substituted cyclopentanones, anti-Markovnikov, ruthenium vinylidene
ID: J48-Y2005-2570
