| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5281757 | Tetrahedron Letters | 2006 | 6 Pages |
The reaction of 1-acetoxy-2,7- and 2,8-enynes with triorganoindium reagents in the presence of 5 mol % palladium catalyst provides cyclic and/or acyclic substitution products depending upon substrate structure. Enynes bearing secondary acetates, quaternary centers, or heteroatoms furnish high yields of carbocyclic or heterocyclic substitution products. NMR studies show that a single trisubstituted alkene stereoisomer is formed in the reaction. A more atom-efficient procedure for the cyclization-substitution process utilizing heteroleptic indium reagents is presented.
Graphical abstractTreatment of acetoxyenynes with triorganoindium reagents in the presence of 5 mol % palladium catalyst leads to the formation of substituted five- and six-membered rings in moderate to high yields.Download full-size image
