Ruthenium-catalysed cross-coupling of vegetable oils with symmetrical alkenes and conversion of the products into diesters and amino esters in tandem sequence reactions

Vegetable oils have been shown to react with 2-butene with very high turnover numbers in the presence of metathesis catalysts to give methyl 9-undecenoate in high yields when a large excess of 2-butene is used. The excess 2-butene can
easily be recovered and reused for several subsequent reactions. Isomerisation, followed by methoxycarbonylation using palladium catalysis can be carried out in the same pot leading to high yields of dimethyldodecanoate.
A related reaction sequences involving isomerisation, hydroformylation hydroamination with benzylamine leads to aminoesters of potential use in the polymer industry.
Reactions of vegetable oils with 1,4-diacetoxybut-2-ene and conversion of the products in to useful synthetic intermediates involving palladium catalysis will also be discussed.