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Grubbs Cross-Metathesis Pathway for a Scalable Synthesis of γ-Keto-α,β-unsaturated Esters

[Image: see text] A direct and scalable route to γ-keto-α,β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs’ second-generation olefin metathesis catalyst for cross-metathesis of alkyl acrylates and 2...

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Detalles Bibliográficos
Autores principales: Nair, Reji N., Bannister, Thomas D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985456/
https://www.ncbi.nlm.nih.gov/pubmed/24393145
http://dx.doi.org/10.1021/jo4023606
Descripción
Sumario:[Image: see text] A direct and scalable route to γ-keto-α,β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs’ second-generation olefin metathesis catalyst for cross-metathesis of alkyl acrylates and 2° allylic alcohols. The metathesis step is followed by oxidation to give the desired products in high yield on scales of up to 25 g.