Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 8, Issue 8, Pages 1786-1794Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201300324
Keywords
alkenes; alkynes; ethers; gold; heterocycles
Categories
Funding
- Deutsche Forschungsgemeinschaft [SFB 623]
Ask authors/readers for more resources
The gold-catalyzed conversion of allyl-(ortho-alkynylphenyl)methyl ethers was investigated, and allylated isochromenes were obtained. An optimization of the catalysis conditions with respect to different phosphane and carbene ligands on gold, different counterions, and different solvents was conducted. Subsequently, the scope and limitations of this reaction were investigated with 21 substrates. The mechanistic studies show an allylic inversion, as supported by NMR data and an X-ray crystal structure analysis, as well as an intermolecular reaction, as determined by crossover experiments. There is no competition of protodeauration even in the presence of water. All these observations differ from other related conversions and clearly indicate product formation by a [3,3]sigmatropic rearrangement in the step forming the new CC bond.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available