Jump to Main Content
Diastereoselective Synthesis of Seven-Membered-Ring trans-Alkenes from Dienes and Aldehydes by Silylene Transfer
- Greene, Margaret
A., Prévost, Michel, Tolopilo, Joshua, Woerpel, K. A.
- Journal of the American Chemical Society 2012 v.134 no.30 pp. 12482-12484
- aldehydes, alkenes, silanes
- Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen–hydrogen bonds across the carbon–carbon double bonds.