Kinetically controlled cross-metathesis reactions with high E-olefin selectivities.
[reaction: see text] Homoallylic alcohols with anti-allylic substituents display enhanced E-olefin selectivity in cross-metathesis (CM) reactions with allyltrimethylsilane. The high selectivity can be explained via a five-membered chelate intermediate in which the hydroxyl group of the homoallylic alcohol coordinates to the ruthenium metal center of Grubbs' catalyst.
Engelhardt
F C
FC
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.
Schmitt
M J
MJ
Taylor
R E
RE