Dialkylaluminum Hydride-Promoted Cyclodimerization of Silylated 1,3-Enynes via Skeletal Rearrangement

The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism involving sequential hydroalumination, alkene is...

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Bibliographic Details
Published in:Organic letters 2011-12, Vol.13 (23), p.6192-6195
Main Authors: Kinoshita, Hidenori, Ishikawa, Tomoyuki, Miura, Katsukiyo
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Alkynes - chemistry
Aluminum - chemistry
Benzene Derivatives - chemical synthesis
Benzene Derivatives - chemistry
Cyclization
Molecular Structure
Organometallic Compounds - chemistry
Silanes - chemistry
Stereoisomerism
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Summary:The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism involving sequential hydroalumination, alkene isomerization, carboalumination, carbon–carbon bond cleavage, and retro-hydroalumination.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202601s