Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E‑Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers
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, wherea...
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| Veröffentlicht in: | Journal of organic chemistry 2016-09, Vol.81 (17), p.7591-7596 |
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| container_issue | 17 |
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| container_title | Journal of organic chemistry |
| container_volume | 81 |
| creator | Lee, Jihong Kim, Kyung Hwan Lee, Ok Suk Choi, Tae-Lim Lee, Hee-Seung Ihee, Hyotcherl Sohn, Jeong-Hun |
| description | 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. |
| doi_str_mv | 10.1021/acs.joc.6b01276 |
| format | Article |
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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.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.6b01276</identifier><identifier>PMID: 27463964</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2016-09, Vol.81 (17), p.7591-7596</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-4f08118653affe2d599512b4034c2aa8da313c67bd1ffd6cf22d8023945424833</citedby><cites>FETCH-LOGICAL-a333t-4f08118653affe2d599512b4034c2aa8da313c67bd1ffd6cf22d8023945424833</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.6b01276$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.6b01276$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27463964$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lee, Jihong</creatorcontrib><creatorcontrib>Kim, Kyung Hwan</creatorcontrib><creatorcontrib>Lee, Ok Suk</creatorcontrib><creatorcontrib>Choi, Tae-Lim</creatorcontrib><creatorcontrib>Lee, Hee-Seung</creatorcontrib><creatorcontrib>Ihee, Hyotcherl</creatorcontrib><creatorcontrib>Sohn, Jeong-Hun</creatorcontrib><title>Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E‑Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers</title><title>Journal of organic chemistry</title><addtitle>J. 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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.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LHTEUhoNU9Fa7dleyLJS55vvOLO1FbcGiaLvpZshNTnDszMTmZCruuuvav-gvaWRuu2sIJITnfQ95CDnibMmZ4MfW4fIuuqXZMC5WZocsuBasMg1Tr8iCMSEqKYzcJ68R71hZWus9si9WysjGqAX5fZUgQILRAY2BXk_5FsZuGqoPFsHTz5BtecEO6dpm2z9iRprjg02efquoHT09ff71dNJ_hxGQ2rLp-dR5oCEmegM9uNz9BHoNtlzi-BKmM01vcpkbO4wDJDwku8H2CG-25wH5enb6Zf2xurg8_7Q-uaislDJXKrCa89poaUMA4XXTaC42iknlhLW1t5JLZ1Ybz0PwxgUhfM2EbJRWQtVSHpB3c-99ij8mwNwOHTroeztCnLDlNTdGas6bgh7PqEsRsWhq71M32PTYcta-2G-L_bbYb7f2S-LttnzaDOD_8X91F-D9DMzJKY3lr_-t-wM98ZFr</recordid><startdate>20160902</startdate><enddate>20160902</enddate><creator>Lee, Jihong</creator><creator>Kim, Kyung Hwan</creator><creator>Lee, Ok Suk</creator><creator>Choi, Tae-Lim</creator><creator>Lee, Hee-Seung</creator><creator>Ihee, Hyotcherl</creator><creator>Sohn, Jeong-Hun</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20160902</creationdate><title>Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E‑Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers</title><author>Lee, Jihong ; Kim, Kyung Hwan ; Lee, Ok Suk ; Choi, Tae-Lim ; Lee, Hee-Seung ; Ihee, Hyotcherl ; Sohn, Jeong-Hun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-4f08118653affe2d599512b4034c2aa8da313c67bd1ffd6cf22d8023945424833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Jihong</creatorcontrib><creatorcontrib>Kim, Kyung Hwan</creatorcontrib><creatorcontrib>Lee, Ok Suk</creatorcontrib><creatorcontrib>Choi, Tae-Lim</creatorcontrib><creatorcontrib>Lee, Hee-Seung</creatorcontrib><creatorcontrib>Ihee, Hyotcherl</creatorcontrib><creatorcontrib>Sohn, Jeong-Hun</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Jihong</au><au>Kim, Kyung Hwan</au><au>Lee, Ok Suk</au><au>Choi, Tae-Lim</au><au>Lee, Hee-Seung</au><au>Ihee, Hyotcherl</au><au>Sohn, Jeong-Hun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E‑Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2016-09-02</date><risdate>2016</risdate><volume>81</volume><issue>17</issue><spage>7591</spage><epage>7596</epage><pages>7591-7596</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>27463964</pmid><doi>10.1021/acs.joc.6b01276</doi><tpages>6</tpages></addata></record> |
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| title | Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E‑Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers |
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