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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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 25; pp. 10357 - 10360
Main Authors Larsen, Casey R, Grotjahn, Douglas B
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.06.2012
Amer Chemical Soc
Subjects
ambient temperature
catalysts
Chemistry
Chemistry, Multidisciplinary
isomerization
Physical Sciences
Science & Technology
stereochemistry
CARBENE
ETHERS
ALLYLIC ALCOHOLS
DOUBLE-BOND MIGRATION
COMPLEXES
IRIDIUM-CATALYZED ISOMERIZATION
BIFUNCTIONAL CATALYST
O-ALLYL
RUTHENIUM
REDOX ISOMERIZATION
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja3036477