Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E-Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers
详细信息 查看全文
- 作者：Jihong Lee ; Kyung Hwan Kim ; Ok Suk Lee ; Tae-Lim Choi ; Hee-Seung Lee ; Hyotcherl Ihee ; Jeong-Hun Sohn
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：September 2, 2016
- 年：2016
- 卷：81
- 期：17
- 页码：7591-7596
- 全文大小：381K
- 年卷期：0
- ISSN：1520-6904
文摘
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.