Stereoselective Alkene Isomerization over One Position
Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for selective mono-isomerization of a variety of multifunctional alkenes to afford >99.5% E-products. Many reactions are complete within 10 min at roo...
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| Published in | Journal of the American Chemical Society Vol. 134; no. 25; pp. 10357 - 10360 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
27.06.2012
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for selective mono-isomerization of a variety of multifunctional alkenes to afford >99.5% E-products. Many reactions are complete within 10 min at room temperature. Even sensitive enols and enamides susceptible to further reaction can be generated. Catalyst loadings in the 0.01–0.1 mol% range can be employed. E-to-Z isomerization of the product from diallyl ether was only <10–6 times as fast as its formation, showing the extremely high kinetic selectivity of 1. |
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| AbstractList | Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for selective mono-isomerization of a variety of multifunctional alkenes to afford >99.5% E-products. Many reactions are complete within 10 min at room temperature. Even sensitive enols and enamides susceptible to further reaction can be generated. Catalyst loadings in the 0.01-0.1 mol% range can be employed. E-to-Z isomerization of the product from diallyl ether was only <10(-6) times as fast as its formation, showing the extremely high kinetic selectivity of 1. Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for selective mono-isomerization of a variety of multifunctional alkenes to afford >99.5% E-products. Many reactions are complete within 10 min at room temperature. Even sensitive enols and enamides susceptible to further reaction can be generated. Catalyst loadings in the 0.01-0.1 mol% range can be employed. E-to-Z isomerization of the product from diallyl ether was only <10(-6) times as fast as its formation, showing the extremely high kinetic selectivity of 1.Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for selective mono-isomerization of a variety of multifunctional alkenes to afford >99.5% E-products. Many reactions are complete within 10 min at room temperature. Even sensitive enols and enamides susceptible to further reaction can be generated. Catalyst loadings in the 0.01-0.1 mol% range can be employed. E-to-Z isomerization of the product from diallyl ether was only <10(-6) times as fast as its formation, showing the extremely high kinetic selectivity of 1. Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for selective mono-isomerization of a variety of multifunctional alkenes to afford >99.5% E-products. Many reactions are complete within 10 min at room temperature. Even sensitive enols and enamides susceptible to further reaction can be generated. Catalyst loadings in the 0.01–0.1 mol% range can be employed. E-to-Z isomerization of the product from diallyl ether was only <10–⁶ times as fast as its formation, showing the extremely high kinetic selectivity of 1. |
| Author | Larsen, Casey R Grotjahn, Douglas B |
| AuthorAffiliation | San Diego State University |
| AuthorAffiliation_xml | – name: San Diego State University |
| Author_xml | – sequence: 1 givenname: Casey R surname: Larsen fullname: Larsen, Casey R – sequence: 2 givenname: Douglas B surname: Grotjahn fullname: Grotjahn, Douglas B email: grotjahn@sciences.sdsu.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22702432$$D View this record in MEDLINE/PubMed |
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| Copyright | Copyright © 2012 American Chemical Society |
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| Keywords | CARBENE ETHERS ALLYLIC ALCOHOLS DOUBLE-BOND MIGRATION COMPLEXES IRIDIUM-CATALYZED ISOMERIZATION BIFUNCTIONAL CATALYST O-ALLYL RUTHENIUM REDOX ISOMERIZATION |
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| Snippet | Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for... |
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| SubjectTerms | ambient temperature catalysts Chemistry Chemistry, Multidisciplinary isomerization Physical Sciences Science & Technology stereochemistry |
| Title | Stereoselective Alkene Isomerization over One Position |
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