Oxasilacyclopentenes were shown to be synthetically useful masked allylic alcohols constructed in high yields and regioselectivities from terminal and internal alkynes. Several functional groups were shown to be tolerated utilizing silver-catalyzed silacyclopropenation of alkynes. In situ insertion of various carbonyl compounds into silacyclopropenes afforded regioselective formation of oxasilacyclopentenes. Elaboration of the oxasilacyclopentenes displayed the synthetic utility of these substrates. Both diastereoselective hydrogenation and Diels-Alder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes.
|Original language||English (US)|
|Number of pages||2|
|Journal||Journal of the American Chemical Society|
|State||Published - Aug 11 2004|
ASJC Scopus subject areas
- Colloid and Surface Chemistry