Spicing up olefin cross metathesis with the renewables estragole and methyl sorbate

Abstract Diene moieties conjugated to a carbonyl group are ubiquitous in nature and are present in compounds with relevant biological properties. Herein we investigate the cross metathesis (CM) of the renewable cross partners estragole and methyl sorbate (MeSo) to produce methyl 6-(4-methoxyphenyl)hexa-2,4-dienoate. By the judicious choice of the ruthenium-based metathesis catalysts, as well as the reaction conditions, it was possible to obtain good conversion and selectivity for the desired product in catalyst loadings as low as 50 ppm (0.005 mol%), with a minimal amount of solvent.