title: Grubbs cross-metathesis pathway for a scalable synthesis of γ-keto-α,β-unsaturated esters.
abstract: 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.
authors.affiliation: Translational Research Institute and Department of Chemistry, The Scripps Research Institute , 130 Scripps Way, Jupiter, Florida 33458, United States.
authors.forename: Reji N
authors.initials: RN
authors.lastname: Nair
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Bannister
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D004952:Esters; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004952:Esters; D007659:Ketones