(Pentamethylcyclopentadienyl)Iridium Dichloride Dimer {[IrCpCl2]2}: A Novel Efficient Catalyst for the Cycloisomerizations of Homopropargylic Diols and N-Tethered Enynes

(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl2]2}‐catalyzed hydroalkoxylation of bis‐homopropargylic alcohols provides an efficient access to dioxabicyclo[2.2.1]ketals. The cycloisomerizations proceed under mild conditions, with low catalytic loadings and short reaction times. This...

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Published in:Advanced synthesis & catalysis 2011-08, Vol.353 (11-12), p.1908-1912
Main Authors: Benedetti, Erica, Simonneau, Antoine, Hours, Alexandra, Amouri, Hani, Penoni, Andrea, Palmisano, Giovanni, Malacria, Max, Goddard, Jean-Philippe, Fensterbank, Louis
Format: Article
Language:English
Subjects:
Alcohols
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
bicyclic compounds
Catalysis
Catalysts
Catalysts: preparations and properties
Chemistry
cycloisomerization
Dichlorides
Dimers
Diols
enynes
Exact sciences and technology
General and physical chemistry
homogeneous catalysis
iridium(III)
Organic chemistry
Preparations and properties
Reaction time
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl2]2}‐catalyzed hydroalkoxylation of bis‐homopropargylic alcohols provides an efficient access to dioxabicyclo[2.2.1]ketals. The cycloisomerizations proceed under mild conditions, with low catalytic loadings and short reaction times. This new protocol involving an Ir(III) catalyst also promoted the cycloisomerization of nitrogen‐tethered 1,6‐enynes to give azabicyclo[4.1.0]heptenes, enhancing the synthetic potential of our method.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201100124