A novel Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans is reported. Mechanistic studies by 13C-labeling experiments confirm oxidative addition of Pt(II) regioselectively to the least substituted carbon-carbon bond of the cyclopropane to form a platinacyclobutane intermediate. To our knowledge, this is the first alkoxy-substituted platinacyclobutane that has been observed spectroscopically. The scope and a proposed mechanism of this new Pt-catalyzed transformation are described. (Chemical Equation Presented).
|Original language||English (US)|
|Number of pages||14|
|Journal||Journal of Organic Chemistry|
|State||Published - May 15 2015|
ASJC Scopus subject areas
- Organic Chemistry