Metathesis of natural products Using Ru-catalysts: surprisingly high selectivity in the reaction of pseudoionone
Metathesis of pseudoionone using Grubbs II and Grubbs Hoveyda II was studied. Reactions was very fast at 110°C (nearly 3 min), with a conversion as high as 90%. Products from self-metathesis and ring-closing metathesis were observed. In spite of the high number of double bonds and isomers (E,Z), a surprisingly high selectivity were observed. With a more diluted reaction, exclusively products of ring-closing metathesis were observed, mesityl oxide (MO) and 1-methyl-cyclohexa-1,3-diene (CHD), with a conversion of 77% and a ratio MO : CHD = 1.5. Using higher concentrations of pseudoionone (favoring self-metathesis), five main products were observed, four products of metathesis and one of isomerization, including alkenes (diene and triene) and unsaturated ketone, mainly because the primary products react very selectively to mainly forming mesityl oxide (MO).