PubAg

Main content area

Diastereoselective Synthesis of Seven-Membered-Ring trans-Alkenes from Dienes and Aldehydes by Silylene Transfer

Author:
Greene, Margaret A., Prévost, Michel, Tolopilo, Joshua, Woerpel, K. A.
Source:
Journal of the American Chemical Society 2012 v.134 no.30 pp. 12482-12484
ISSN:
1520-5126
Subject:
aldehydes, alkenes, silanes
Abstract:
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.
Agid:
5386218