Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer.

Autor: Greene MA; Department of Chemistry, New York University, New York, New York 10003, United States., Prévost M, Tolopilo J, Woerpel KA
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2012 Aug 01; Vol. 134 (30), pp. 12482-4. Date of Electronic Publication: 2012 Jul 20.
DOI: 10.1021/ja305713v
Abstrakt: 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.
Databáze: MEDLINE