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Isomerization of Olefins Triggered by Rhodium-Catalyzed C-H Bond Activation: Control of Endocyclic β-Hydrogen Elimination.

Yip SY, Aïssa C - Angew. Chem. Int. Ed. Engl. (2015)

Bottom Line: The rhodium-catalyzed isomerization of 4-pentenals into 3-pentenals occurs through this elementary step and cleavage of two C-H bonds, as supported by deuterium-labeling studies.The reaction proceeds without decarbonylation, leads to trans olefins exclusively, and tolerates other olefins normally prone to isomerization.Endocyclic β-hydrogen elimination can also be controlled in an enantiodivergent reaction on a racemic mixture.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Liverpool, Crown Street, L69 7ZD (UK).

No MeSH data available.


Deuterium-labeling experiments.
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sch01: Deuterium-labeling experiments.


Isomerization of Olefins Triggered by Rhodium-Catalyzed C-H Bond Activation: Control of Endocyclic β-Hydrogen Elimination.

Yip SY, Aïssa C - Angew. Chem. Int. Ed. Engl. (2015)

Deuterium-labeling experiments.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4497606&req=5

sch01: Deuterium-labeling experiments.
Bottom Line: The rhodium-catalyzed isomerization of 4-pentenals into 3-pentenals occurs through this elementary step and cleavage of two C-H bonds, as supported by deuterium-labeling studies.The reaction proceeds without decarbonylation, leads to trans olefins exclusively, and tolerates other olefins normally prone to isomerization.Endocyclic β-hydrogen elimination can also be controlled in an enantiodivergent reaction on a racemic mixture.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Liverpool, Crown Street, L69 7ZD (UK).

No MeSH data available.