- Journal
- SYNTHESIS-STUTTGART
- Année
- 2016
- Volume
- 48
- Numéro
- 19
- Pages
- 3165-3174
- Mois
- OCT
- DOI
- 10.1055/s-0035-1561486
Abstract
Methoxymethyl ethers derived from 2-(dimethylphenylsilyl) cycloprop-1-enyl carbinols undergo gold-catalyzed rearrangement leading to [(Z)-(dimethylphenylsilyl)methylene]cyclopropanes in moderate to high yields with methyl formate as a byproduct. This transformation proceeds by initial regioselective ring opening of the three-membered ring leading to an alpha-silyl vinyl gold carbenoid. This latter organogold species evolves by 1,5-hydride transfer, which triggers subsequent rearrangement involving loss of methyl formate, 2 pi-electrocyclization of the resulting allylic cation, and elimination of the metal to regenerate the catalyst.