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Synfacts 2008(12): 1322-1322
DOI: 10.1055/s-0028-1083591
DOI: 10.1055/s-0028-1083591
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New YorkRu-Catalyzed Selective Redox Isomerization of Propargylic Alcohols
Contributor(s):Paul Knochel, Andreas J. WagnerB. M. Trost*, R. C. Livingston
Stanford University, USA
An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes
J. Am. Chem. Soc. 2008, 130: 11970-11978
Stanford University, USA
An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes
J. Am. Chem. Soc. 2008, 130: 11970-11978
Further Information
Publication History
Publication Date:
20 November 2008 (online)
Key words
ruthenium - indium - isomerization - propargylic alcohols
Significance
The authors report a novel method for performing the isomerization of propargylic alcohols in high yields to selectively provide (E)-enals and enones using a readily available catalyst. A propargylic hydride migration-based mechanism has been suggested in deuterium-labeling experiments.
Comment
With catalyst loadings as low as 1%, this new protocol constitutes to date the most effective method to redox isomerization of propargyl alcohols with extraordinary selectivity. The cost of Ru compared to Rh makes the use of such Ru catalysts attractive.