Enyne Cross Metathesis

Enyne Cross Metathesis-34
L’exploration de la métathèse croisée de nitriles insaturés bio-sourcés avec des acrylates a conduit à des dérivés d’α,ω-amino acides, tandis que les aldéhydes gras ont permis un accès rapide à des aldéhydes bifonctionnalisés à longue chaîne et à des diols saturés.Deux voies d’accès à des diènes conjugués fonctionnels impliquant des réactions de métathèse catalysées par le ruthénium à partir d’oléfines issues de la biomasse sont décrites : l’une par métathèse croisée avec un alcyne, l’autre par métathèse croisée avec un chlorure allylique suivie d’une réaction de déhydrohalogénation catalytique.

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Within this trend, the use of renewable unsaturated vegetable oils is attractive [1-4].

Catalytic olefin metathesis has a strong potential for selective biomass transformations.

Cross metathesis between silylalkynes and various functionalized alkenes catalyzed by Grubbs carbene complex produced, in most cases, single regio- and stereoisomers of the resultant 1,3-dienes.

Polar heteroatom substituents at the propargylic site are important for high reactivity and selectivity.

An efficient and stereoselective synthesis of d,l-gulose was described.

The key step of the synthetic route is represented by a multicomponent enyne cross metathesis—hetero Diels–Alder reaction which allows the formation of the pyran ring from cheap and commercially available substrates in a single synthetic step.

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Two ways of access to functional dienes by ruthenium-catalyzed ene-yne cross-metathesis of plant oil alkene derivatives with alkynes and by cross-metathesis of bio-sourced alkenes with allylic chloride followed by catalytic dehydrohalogenation, are reported.

Ricinoleate derivatives offer a direct access to chiral dihydropyrans and tetrahydropyrans via ring closing metathesis.


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