Substituent effects on the Z/E-selectivity in cross-metathesis of conjugated enynes

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Cross-metathesis of a range of conjugated enynes with alkenes turns out to proceed with preferential formation of Z-isomers over E-isomers up to >25:1. Careful studies including substrate modification and control experiments revealed that the reaction proceeds under kinetic rather than thermodynamic control. Driving forces for this substrate-dependent Z-selectivity are attributed to the steric hindrance between substituents on the reacting enynes and NHC ligand of the ruthenium catalyst in the putative metallacyclobutane, as well as chelation effects of suitably positioned functional groups to Ru, which is strongly supported by ab initio calculations.
Publisher
AMER CHEMICAL SOC
Issue Date
2004-10
Language
English
Article Type
Article
Keywords

CATALYZED OLEFIN METATHESIS; RUTHENIUM CARBENE COMPLEXES; RING-CLOSING METATHESIS; CONCISE SYNTHETIC ROUTE; THEORETICAL PERSPECTIVE; BASIS-SETS; MECHANISM; EFFICIENT; ACRYLONITRILE; MODEL

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.69, no.22, pp.7661 - 7664

ISSN
0022-3263
DOI
10.1021/jo048883q
URI
http://hdl.handle.net/10203/82947
Appears in Collection
CH-Journal Papers(저널논문)
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