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. 2011 Dec 2;13(23):6192-5.
doi: 10.1021/ol202601s. Epub 2011 Nov 1.

Dialkylaluminum hydride-promoted cyclodimerization of silylated 1,3-enynes via skeletal rearrangement

Hidenori Kinoshita  1 , Tomoyuki Ishikawa, Katsukiyo Miura
Affiliations

Dialkylaluminum hydride-promoted cyclodimerization of silylated 1,3-enynes via skeletal rearrangement

Hidenori Kinoshita et al. Org Lett. .

Abstract

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.

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