Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E-Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers
SCIE
SCOPUS
- Title
- Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E-Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers
- Authors
- Jihong Lee; KIM, KYUNG HWAN; Ok Suk Lee; Tae-Lim Choi; Hee-Seung Lee; Hyotcherl Ihee; Jeong-Hun Sohn
- Date Issued
- 2016-09-02
- Publisher
- AMER CHEMICAL SOC
- Abstract
- 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.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/94132
- DOI
- 10.1021/acs.joc.6b01276
- ISSN
- 0022-3263
- Article Type
- Article
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 17, page. 7591 - 7596, 2016-09-02
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