Grubbs cross-metathesis pathway for a scalable synthesis of γ-keto-α,β-unsaturated esters.
J Org Chem, 2014/2/07;79(3):1467-72.
Nair RN[1], Bannister TD
Affiliations
PMID: 24393145DOI: 10.1021/jo4023606
Impact factor: 4.198
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.
MeSH terms
Biological Products; Catalysis; Chemistry, Pharmaceutical; Esters; Ketones; Molecular Structure; Oxidation-Reduction; Stereoisomerism
More resources
Full text:
Europe PubMed Central; PubMed Central
EndNote: Download