Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E-Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers

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As a guide for selective reactions toward either Z- or E-alkene in a metathesis reaction, the relative preference of metathesis Ru catalysts for each stereoisomer was determined by a method using time-dependent fluorescence quenching. We found that Ru-1 prefers the Z-isomer over the E-isomer, whereas Ru-2 prefers the E-isomer over the Z-isomer. The Z/E-alkene preference of the catalysts precisely predicted the Z/E isomeric selectivity in the metathesis reactions of diene substrates possessing combinations of Z/E-alkenes. For the diene substrates, the rate order of the reactions using Ru-1 was Z,Z-1,6-diene > Z,E-1,6-diene > E,E-1,6-diene, while the completely opposite order of E,E-1,6-diene > Z,E-1,6-diene > Z,Z-1,6-diene was exhibited in the case of Ru-2
Publisher
AMER CHEMICAL SOC
Issue Date
2016-09
Language
English
Article Type
Article
Keywords

RESONANCE ENERGY-TRANSFER; RING-CLOSING METATHESIS; STEREOSELECTIVE OLEFIN METATHESIS; HETEROCYCLIC CARBENE LIGANDS; CROSS-METATHESIS; OPENING/CROSS-METATHESIS; ENYNE METATHESIS; TERMINAL OLEFINS; RU CARBENES; COMPLEXES

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.81, no.17, pp.7591 - 7596

ISSN
0022-3263
DOI
10.1021/acs.joc.6b01276
URI
http://hdl.handle.net/10203/213507
Appears in Collection
CH-Journal Papers(저널논문)
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