Cross-metathesis of methyl 10-undecenoate with dimethyl maleate: an efficient protocol with nearly quantitative yields

Functionalization of (-)-β-pinene and (-)-limonene via cross metathesis with symmetrical internal olefins

“…This result contrasts with the easy formation of cross metathesis products from acrylic acid esters as well as maleate by cross metathesis with non-sterically hindered monosubstituted terminal olefins [23,24]. Indeed, maleates and fumarates have been efficiently used in olefin cross metathesis in place of acrylates, especially with the objective of reducing the number of possible cross metathesis products, but they had never been shown to be suitable substrates when acrylates did not work.…”

Alkene Metathesis for Transformations of Renewables

“…It was demonstrated that at 80 °C in toluene, the cross metathesis with methyl acrylate was faster and required lower catalyst loading (0.5 mol%) than the cross metathesis involving dimethyl maleate. [118] Scheme 25 CM of methyl 10-undecenoate 72 with diethyl maleate 73…”

A Combined Bio-Chemical Synthesis Route for 1-Octene Sheds Light on Rhamnolipid Structure

“…Ruthenium-based carbene catalysts (so-called Grubbs catalysts) in combination with modified Grubbs−Hoveyda-type catalysts allow transformation of such olefins with a broad variety of functional groups present [22]. Olefin metathesis offers synthesis pathways to convert biobased substrates such as oils and fatty acids into fine chemicals and fuel components, explaining the considerable interest in this reaction [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40].…”